I just finished going through a job search cycle and realized it was time to update my interviewing post. This is what I would have gone back and told my six-months-ago self.

  1. Repeat until satisfied:
  2.     Apply
  3.     Prepare
  4.     Interview
  5.     Recover

Step 1. Repeat until satisfied

Know what you want

It can be surprisingly hard to get a clear idea of what you want. Money is useful and there's a number attached to it, so it's easy to focus on compensation. But it's useful to remember that's just one ingredient in the stew. There are a lot of other things that will determine how satisfying the job will be and how it will affect the trajectory of your career. A few others that were high on my list were work-life balance, the option to work remotely, and a stable company vision.

Your list will look different, but whatever it is, write it down. Nail down your "would be nice", your "strongly prefer" and your "non-negotiable" points. Once the interviews start, it can be easy to get swept up in the moment and settle for a position that you don't really want. It's especially tough if you get caught at a low point and see an opportunity to put a stop to the interviewing grind. Writing down your list lets you reach forward in time and support tired, discouraged, disoriented future you. Future you will be really thankful.

I had to go through a couple of interviews before this list got crisp for me. Being forced to choose between what I wanted versus what I needed in practice is different than doing it in the hypothetical. Your list may evolve over time too. That's great. Just keep it in writing so you can hold yourself to account when making decisions.

Don't stop

This approach is not guaranteed to help you land a particular job, but it will absolutely help get you into a job you're satisfied with. “In the end, everything will be ok. If it's not ok, it's not yet the end." (Fernando Sabino, popularized by John Lennon, from an Indian proverb.) Tautologically, you will eventually find a place you are content with if you don't stop looking until you find it.

It's tempting to stop looking after you get several rejections. You might start to think that you aren't qualified for what you want and need to settle for something else. Don't stop. There are a hundred reasons you might not get an offer that you are perfectly qualified for. You can't foresee them all or control them. You'll drive yourself mad if you try. Just keep interviewing. You'll probably get told no a lot, or worse, get told nothing. Move on to the next company on the list.

My mental model of the job hunt is that success half depends on my qualifications and half depends on a roll of the dice. I can increase my chances of getting an offer by learning another skill, but there is a huge component that is pure chance. A "no" doesn't mean you're not qualified. It just means this position on this day isn't for you. Don't stop. Oliver Goldsmith (an Irish writer in the 1700s) said "Success consists of getting up just one more time than you fall." Getting up is hard, and we'll revisit that in step 5. But if you can manage it, getting up guarantees that you'll win eventually.

Step 2: Apply

Make a short list

I don't have any deep insights here. Consider as many sources as you can. There's no one channel for finding open position. Talk to your friends, acquaintances, and former colleagues. Follow up on the recruiter emails you've been deleting. Talk a walk through LinkedIn's job postings. Go to websites of companies you've heard of and comb their job postings. Keep your eyes open.

Don't worry about checking every box

Keep in mind that job postings are sometimes written by someone other than the person who will be making the hiring decision. Or sometimes the post is written as a wishlist, rather than hard constraints. Or sometimes the company's needs change between when the post goes up and when you interview. They do their best, and the posting is a very useful guide, but don't feel like you absolutely have to have every skill and experience in the bullet list.

You'll never feel 100% prepared or qualified. I've never met all the requirements in a job posting. There are always huge (to my eyes) gaps between what the posting is asking for and what I have. There's just too much to know, too many things to memorize, too many tools to learn. But get as close as you can. If the posting asks for experience with Tableau and you've never touched it, mention all your experience with dashboards and visualizations in other tools. It will be tempting to lie, at least a little bit. Don't do it. It's not worth it. But absolutely say all of the true things as loudly and clearly as you can.

Customize your Resume

I take a careful look at my resume each time before I submit it. I rephrase it to include terms and tools from the job posting. If the posting lists "recommender systems" and my resume mentions a "collaborative filter" I built, I'll change mine to match. Often the first person reading your resume won't be able to recognize that a collaborative filter is a recommender system, so you're helping them out. It's a superficial tweak. You're still saying a lot of true things. You're just phrasing them so that they take absolutely no mental leaps to fit it to the job posting.

You can also change the order of items to put the most relevant closer to the top (say in a Skills section) or to expand on project work that is particularly relevant. If you send a different resume to every potential employer, it's a sign that you are serious about showing how well you can give them what they want.

Pace yourself

The job hunt can take a lot of time and attention, especially once the interviews start. If you're doing it while still holding down another job and other responsibilities, you can manage the disruption by dribbling out your applications one or two at a time. The downside of this is that it can take a while. My most recent cycle was six months from first responding to a recruiter's email to signing the offer. If you are lucky enough to have this kind of flexibility it can be a good way to hang on to your sanity.

Step 3. Prepare

There's a little bit of overlap between the skill it takes to interview well and the skills it takes to do a job well, but not as much as you'd think. Preparing for an interview is a different type of thing than learning the technical and management skills you'll need day to day. It's a separate game with its own rules that nobody tells you (mostly because no single person knows them) and the best we can do is go in with our eyes open and mind fresh.

Read about the company

If you walk into an interview already having a general idea of where the company is getting its money, what kind of data they are working with, and what types of technical problems are important to them, you will stand out from the other applicants. It will look like you studied some of the interview questions beforehand. There is a surprisingly detailed trove of information about companies online.

Glassdoor is useful for taking the temperature of employee morale and estimating what your compensation would be. levels.fyi is another source of compensation info for a few software and data positions for a few large companies. Some companies publish engineering blogs or give recruitment talks at conferences. And an hour or two of Google stalking can give a good sense of the company's recent achievements and stumbles.

Talk to people you know

If you know someone who works or has worked at the company, see if you can talk with them for a few minutes to learn more about it. That can tell you some pretty important things that you couldn't easily learn any other way.

Read about the interviewers

If you're lucky enough to get the names of your interviewers beforehand, get to know them digitally too. They will be reading your resume. Visit LinkedIn and read theirs. Pay special attention to what they do in their current position. Their past companies and projects can also give insight into what types of questions they're likely to ask. Don't overdo it here. It's safest to stick to information they've published about their professional activities. But taking a moment to get a sense of who they are will help smooth the way for your conversation with them.

Focus on weak spots

Look through the posting and take note of the bullet points that make you cringe. Maybe you've never heard of the Flamy Framework or worked in W++. Do a little research to find out what all the words mean. Maybe read an article or watch a video. Most importantly spend a minute to connect them to your own experience so that when you get asked about your experience with them, you can explain that you haven't used that particular framework, but you've used one that kind of does the same thing, and then you can take the conversation into a place where you can showcase your knowhow.

I like to spend some time on whatever questions I got stumbled on or was stumped by in my last interview. Sometimes if I'm feeling particularly burnt about it, I'll write a post to my past self describing the topic in painful detail. Otherwise, a Wikipedia skim and a couple of notes are enough to set me up to say something more helpful if I get the question again.

Don't get down on yourself for not knowing everything. No one does. Absolutely no one. Your goal here is just to buy a little familiarity so you know how everything fits together, not to become an expert.

Focus on strong spots

For all the bullet points you feel confident with, it's helpful to think through how you'll talk about it. A thirty second story about how you used anomaly detection in a project is more powerful than just explaining the concept behind it. I've found that building a small list of mini-stories about project work that I've done is a useful way to communicate my strengths. This is especially true for interview questions aimed at collaboration and leadership.

Step 4. Interview

Oddly, by the time I get to the day of the interview, I find there aren't many big decisions to make. All my strategy is in motion and has been for weeks. All that's left is for it to play out, to turn the crank on the machine I've built. There are a few details I like to keep in mind that tilt the playing field ever so slightly in my direction.

Stack the deck in your favor

Sleep as much as you can for a couple nights prior, eat healthy and plenty, have an emergency snack handy, remove other distractions and responsibilities as well as you can.

You won't know everything

You're going to be stumped. Your interviewer is going to ask you about something you've only heard of and have got only the foggiest idea for how it works. That's OK. It's how the process is supposed to work. If the interviewer doesn't probe deep enough to find your limitations, they're not doing their job. So have a strategy for when this happens.

What works best for me is to talk about what I know that's related: "I don't recall the equation for calculating correlation, but I know it's related to the square of the distance of the points from a best-fit line." Or to explain how I would go about filling that gap in my knowledge: "I haven't had the opportunity to code up a tokenizer from scratch, but I'd start with these three simple methods and then branch out into more complex approaches from there." If it's a puzzle I don't know how to solve, I talk the reviewer through my trial-and-error thought process as I work through it.

What does not work for me is to guess or to exaggerate. Wanting desperately to please an interviewer makes it tempting to tell them what you think they'd like to hear, even if it isn't strictly true. Steer well clear of this. It is far more likely to hurt you than to help.

Keep your head in the game

I can never tell how well an interview went based on my gut feel. During an interview it’s common to feel like you are bombing it, especially when you are stressed and exhausted already. This is normal. It doesn’t mean that you’re actually bombing it. It’s a valuable interviewing skill to keep a level head and continue doing your best. Don’t give up. Keep fighting, no matter how much of a flail it feels like. You may not be able to rescue a rough interview with overly positive thinking, but you can tank an otherwise fine interview by prematurely declaring defeat.

Keep in mind that most interview processes have a little bit of wiggle room built-in. Good processes expect that there will be noise, that not all of their interviewers are experts yet, that you can have a mental hiccup. Even if you’re not thrilled about how one or two of your interviews go, keep giving the process your best effort. In my experience it’s impossible to know how it’s all going to turn out until you get to talk with the recruiter on the other side of it.

You're also interviewing them

Remember the list you made of what you want out of your next job? Now is a great time to learn about them. I like to have a handful of questions written out so that when the interviewer asks me in the last three minutes whether I have any questions for them, my exhausted brain doesn't have to do too much work. There are a few questions that tend to tell me a lot about what it's like to work there. Can you tell me about a project you worked on that was particularly satisfying or that you are proud of? About how many hours per week of recurring meetings do you have? Where do the ideas come from for the projects you work on? You and your colleagues? Senior management? You can also ask directly about policies and benefits you're concerned about.

Interviewing is the best way to train for interviewing

While interviewing, I've learned a lot of lessons about interviewing. What I learned is probably specific to my field, my background, my personality, and the companies I was talking to. Undoubtedly you will learn some patterns and tricks of your own that are different from mine. It's hard-earned, but more valuable than any training you can buy. I don’t know of a more effective way to pick up these lessons than interviewing.

When you finally land a position, all the interviews you did up to that point will be the training that helped you get there.

Step 5. Recover

Don't skip the recharge

Every step of this process is grueling. To keep up your energy and spirits for the long haul, you'll need to take time to recover. When you can't bring yourself to read another job posting, when you dread opening your inbox, when you're starting to think maybe you're not cut out for the position you want, these are signs that your tank is low and you need to refill.

Deep recharging looks different for everyone, and you might have to learn what it looks like for you. I like to take a couple days or weeks away from the job search and spend time watching TV with my family and treating myself to gratuitous bowls of Grape Nuts. You don't need to be productive or growing or hustling or branding. Just take some time to retreat and do the things that build you back up.

You don't have to wait until after an interview to do this. It's even more effective when you sprinkle it throughout the process whenever you're feeling run down. I know it's working when my mind naturally gravitates back to the search and starts planning my next move or I feel a bit of excitement at the prospect of a new position.

Getting Real

So far, this job search methodology has made one HUGE assumption. Finding a job that you really like is straightforward enough, but it can take a lot of time and a mountain of emotional energy. Those are luxuries that not everyone has. There are common situations that can really hit our time and energy reserves. Caring for a child or a parent. Physical disability or illness. Keeping the cupboards full and the lights on. A toxic workplace. Paying medical bills. Juggling depression, anxiety, and existential despair. Being subjected to harassment and discrimination. If you don’t have unlimited time and energy to spend on it, you might have to cut corners and take a position that’s good enough, at least for now. I wish it wasn’t this way.

[Note to Hiring managers and human resources executives: if you are looking for ways to cut corners, to find less expensive labor, to get someone to do the same work for less money, you are actively taking advantage of those with fewer resources, less bargaining power, and fewer options. It may look good on the company’s balance sheets in the short term. But it doesn’t look good for the company in the long term. It will hurt your people, your product, and your brand. The antagonism of treating your employees as sources of effort from which to juice productivity at minimal cost is 19th-century thinking and deserves to be left there.]

Remember who you are

Interviewing often requires you to be someone you’re not. Not in a deceptive way, but in emphasizing the very best aspects of yourself, the skills you are the strongest in. When we interview we try to be the person that we think the interviewer wants to hire. We emphasize our enthusiasm, our energy, our passion, our knowledge. We play down our fear, our confusion, our frustrations, and our mistakes. As a result we can feel like we are pretending to be someone we aren't. This is bad for the soul and exacts a high toll. If I do this for too long, I can start to forget my center. I start to confuse who the interviewer wants me to be with who I want to be. Watch out for this. No one can tell you who you are or change who you are except you. If we forget this we lose our center, and after that nothing else matters very much.

I don’t know how to avoid this destabilizing force. It is part of the weird game that is interviewing. But I find it helpful to acknowledge that it costs me a lot of mental and emotional energy to interview. I give myself space to be exhausted afterward and am even more generous in granting myself time to recover.

Probably get rejected

Most of the time, even after all of that work, the answer is going to be "no thanks". In my most recent job search I interviewed with 5 different companies before I found my match. There were more nos than yesses. This is a blow to the spirit every time. It is a real injury, even though it's invisible. It takes time to heal. Give yourself that time.

If you can beg a little feedback, get it. It's uncommon, but sometimes the recruiter will let you know what concerns the interviewers had. Their concerns will probably feel unfair and unwarranted. Resist the impulse to explain why or to justify yourself. Graciously accept the feedback and set it aside for your next round of preparations. Then take a good long break doing whatever takes your mind off it.

Maybe get an offer

Do your happy dance, your fist pumps, your primal screams of victory. You did it! Let your pride in a strong performance and your gratitude to the fates of the job search wash over you. A job offer is a tremendous victory.

Don’t say yes.

At least not yet. Say thank you and get as much information as you can. Ask any questions that you haven’t gotten answers to yet. Tell the recruiter that you will get back to them soon. If they put pressure on you to answer immediately or in an uncomfortably short timeframe, that is a bright red flag.

Sit with it

An overwhelming surge of emotion, positive or negative, is not a good place to make a decision that will affect the next years of your life. Give it a chance to cool. Sleep on it. Talk it through with a couple of people you trust. Go for a walk. And when you feel that you’re settling on decision, give it just a little bit longer let that comfort solidify.

Revisit your list of what you want–the one that you wrote down so that you wouldn’t forget what you were shooting for. If you’re lucky, a good offer will have most of the things on the list, but probably not all of them. You may have to do some soul searching and reevaluate just how important the missing items are. Take all the time you need here. Watch for the feeling of things clicking into place, of feeling right. This is different from feeling ecstatic or having it feel easy. But listen for that internal click of things aligning and settling into place. For me this happens when I stop trying to force things to be one way or the other and relax and watch where they naturally want to fall.

Maybe reject the company

It's possible that a company may make you an offer, even a generous one, that just doesn't feel like the right fit. Your gut feel trumps everything else here. You may find yourself in a position where a job offer ticks every item on your list, but you still feel weird about it. Maybe it was something about the interactions during the interviews. Maybe it was something that you’ve learned about the company. Whatever it is, you don’t even need to have a good reason for it, you don’t need to justify it, you don’t even need to be able to put it into words. If you can't shake the feeling of trying to put on a jacket that's two sizes too small or if you are repeating to yourself "I can make this work", then it might be good to let this opportunity go. That feeling is some part of your brain telling you that this is a bad idea.There are other companies who will want you. A better fit will come along. Take a deep breath, look past your interviewing fatigue, thank the recruiter for their help, and move down your list.


This is not something I’m good at, but it's important. I highly recommend you read what Patrick McKensie has said about it.

Putting this all together, here's the recipe that worked for me.

  1. Repeat until satisfied:
  2.     Apply
  3.     Prepare
  4.     Interview
  5.     Recover

I hope some variation of it makes your life a little easier the next time you go through the process.

Best of luck to you!