Notes on landing your next job
16 min read

Notes on landing your next job

A no-bullshit (but hopefully helpful) review of concrete and actionable mistakes, tips, and pointers I have from interviewing 200+ people for product roles - and landing a new job myself.


I recently went back into the job market (in the middle of a recession) and found it to be f***ed up enough to deserve some notes from the field.

If you're a fresh graduate looking for a role in the middle of the first truly global pandemic, a professional with some years under the belt looking for a better challenge, or one of the many people that were unfortunately laid off as part of the Corona Layoffs, I hope my experience helps you land the job you deserve!

And also, if you're a recruiter or an HR person trying to do your candidates and company right during these turbulent times: there's some good tips in here too!

Looking for a job: my story

In mid 2020 I was lucky to have a job which I absolutely love. Every day was incredibly fun and interesting, my colleagues were great, and the company itself was doing amazing.

So why look for a different job? I joined my company at a different time, and with the company growing so far into the stratosphere after the IPO, after more than 2 years I felt I was ready to go back to a more early stage company.

So I looked at the fintech sector, chose what in my opinion was 'the best' company in a certain vertical, and applied for 10 companies. To my surprise, 8 wrote back:

The rest of the article just talks about general tips and lessons I learned during this time. I hope this helps you!

Looking for a job: your story

Before we even start with general tips and takeaways, here's three facts you need to tattoo on your forehead when searching for a job:

  1. Most candidates are incompetent. This is not meant negatively: most candidates applying for a job do not have the necessary competences. I'm not talking about '2 years of experience where the job says 3' - I'm talking marketing managers applying for programming jobs, or programmers applying for data analyst positions. In my experience, up to 50% of applications for any given positions are not even remotely close to the position's requirements. Gotta thank Linkedin EasyApply for that, I guess.
  2. Many candidates are bad. Now, this is meant negatively. There's a lot of candidates that are good on paper (i.e. right experience and past roles), but would actually not be a good fit for the job. Put in serious work, learn fast, ship fast, and you will earn much more experience than your senior colleagues with double as much tenure on paper that are just coasting by on minimum effort. Those tenure coasters unfortunately also apply for jobs - and they are bad candidates.
  3. But HR doesn't know which candidate you are. If you're wondering where I'm going with this: it's hard for your prospect company to know if you're a competent, good candidate. Your goal is to make it as easy as possible for them to put you in the good bucket and hire you. Which leads us nicely into the first tip:

Note 1: skip the great HR filter

Your job hunt starts with an Human Resources (HR) guy or lady scrolling through a new batch of candidates. Most job tracking applicants interfaces (ATS) look like this:

this, times 30 pages

This primordial soup of applicants stretches through multiple pages. Your aim is to stand out to this anonymous, idly scrolling, HR person. You will find thousand of articles on how to do that, and they are all lies. There's basically only three ways to stand out during ATS screening:

  1. Someone told me you were coming. Either a colleague, a good friend, or your mom with whom I go to church told me you're the perfect candidate for this job I just opened. This is called a referral and can be done in two ways: low quality referral (just throw the CV in the pile and the ATS will say 'referred by XXXX'), or high quality referral (your referrer explained to me why you'd be great for my position and handed me an annotated CV or written explanation I can discuss with the team).
  2. You're an internal transfer. Self-explanatory: you already work at the company and are asking to move to my team.
  3. You were head-hunted. Also self-explanatory: the position was opened for you specifically.

You can see what these shortcuts have in common: Neither of these applicants went through the anonymous scrolling HR person. So here's the first note: the best way to get a job is skipping the great HR filter altogether. Try getting a referral or get someone at the company to care.

Note 2: fix yo' CV

If this doesn't sound very democratic, it's because it isn't. This is just the shortcut. Normal people, like me, don't have referrals and still get jobs. To get a job without referrals, you need to fix yo CV and yo motivation letter.

I've seen very many abominations in terms of CV and even worse things when talking motivation letters. Here's 3 key takeaways:

  • βœ… yo' CV should only have relevant experience listed. If you're looking for a job as 'product manager' every single experience better have 'product' in either title or description. Your CV should be about what you want to do, so make it count.
  • βœ… job experiences on yo' CV should have a small description telling HR what you did. PM at a startup is different than PM at Google. Explain your achievements in a way that makes HR think 'oh wow, he/she could be doing this at my company'!
  • βœ… yo' CV should be one page. You only have a few seconds of HR attention. 2-3 pages is insanity. And if you use the abominable Europass CV format and send a 14 pages monster, yo' deserve no job.

For motivation letters just one take-away:

  • βœ… yo' think you can outsmart HR by using a copy-pasted motivation letter with the name of the company you're applying for replaced into it. But yo' can't and yo' won't.

My advice: write something really specific about the company and your future role at it. A copy-pasted motivation letter is indeed a formality no one cares about. But a tailor-made motivation letter explains what you can do for them and gets HR thinking.

Your CV (and, at smaller companies, motivation letter) should have one goal and one goal only: explain to HR what you can do for the company/team you're applying to, so you get moved to the next stage: the actual hiring committee.

Note 3, 4 and 5: the hiring process

I have no tips on how to interview. Your goal is not to turn yourself into the 'ideal' candidate by telling people whatever they want to hear (competent companies with competent interviewers will see right through this type of candidate). No; your goal is to present what you can do for them and show that you're nice to work with.

I do, however, have three very important tips on the hiring process:

note 3: Stick the landing 🎯

Getting past the HR screening means nothing if you don't actually match with the expectations the actual hiring manager had for the role.

The aim should be getting to an early understanding of what the company needs. They are hiring a Product Manager - ok, but to do what? What's the problem they are trying to solve? Why can't they fill that position internally, or ship with their current resources?

I've interviewed a lot of people that just talk about their past experience, their expectations for the job, and generally repeat what I saw on the CV.

I recommend instead to use the time you have to talk to the interviewer and understand why they are trying to hire someone in the first place.

This does three things:

  1. it puts you in a better position to negotiate later on (when you understand which part of your experience and skills they need, and how rare they are in the market),
  2. it helps you in understanding if you really get what you're applying for (maybe the description was great, but you would hate your job if they hired you!)
  3. Even if the position you're interviewing for leads to no offer, your interviewer might be positively impressed and refer you for another position internally! (see tip #1)

note 4: Ask the hard questions. Bring the hard answers.

When I was on hiring committees, candidates would go out of the way to tell me how great the company is. That's par for the course: I sure hope that you only apply to companies you like - so there's no point in telling your hiring manager that everything the company is doing is perfect.

Conversely, no one likes a know-it-all that tells them their company sucks and the only way to fix it is to hire them. Arrogance is a very fast reject.

In your hours of interviews you should try to walk a fine line between flattery and challenge, and keep the information density high. Don't just tell them things you both know (your CV, your life), and save a couple softball questions for the end of the interview. Instead, work together with your interviewing committee. Read up on the company and their competitors. Why does competitor X have feature Y, and the company you're applying for doesn't? This can lead to very challenging discussions (I would usually ask, 'ok, how would you develop feature Y?').

But here's the thing. Assuming you're interviewing with smart people, they have figured out the hard questions already. Probably they have been trying to launch 'feature Y' for the past year(s). If you can demonstrate you can see the need for Feature Y in just a short interview, you're basically showing you can be part of the crew. And if you can get anywhere close to a real answer, you're probably hired or referred internally to the team with the hard question you solved. Believe me, I've seen this happen.

note 5: Get me the president πŸ“ž

This is a short one. If you're the leader of a foreign country, and you get invited to the White House, and you don't get to see the President and his or her circle - then chances are the White House isn't that interested in whatever you do, or that you're not a strategic ally.

Similarly, if you're interviewing for a senior position, and you're not seeing the key leaders for that position, you're probably not interviewing for a senior position regardless of what the title says. If you're interviewing as a PM and you only see Support and Ops people, I can 100% guarantee you this isn't a PM position. And so on.

In the middle of a recession you might be under pressure (financially, personally, or both) to get a job ASAP, so now you might be thinking 'wow this is such a minor nitpick'.

But it really isn't: by applying for a certain role you're setting expectations both for yourself and the hiring party. I can guarantee you that companies that don't care about you during the hiring process will not magically start caring for you after they hire you.

Good companies will always plan an interview round with either a senior person, a VP/director, or a C-suite (depending on the role's seniority - junior, medior, senior). If they don't, ask for it and see what happens. If you want to understand how important the role is, make sure you talk to your President πŸ“ž

Note 6, 7: landing an initial offer

At a certain point in your interview journey, you get to the end of it. This will take a few weeks in total - more weeks the more senior the position and the more stringent the hiring requirements.

Companies wrap up the hiring process in two different ways:

  1. The 'optimal stopping' company will extend an offer to the first adequate candidate that finishes the interview process. This company knows talent is scarce and usually has multiple positions open, so they will reroute the other candidates interviewing for the same position to other roles internally, or extend them an offer progressively if you refuse yours.
  2. The 'fairest of them all' company will first wait for all candidates to finish the process, rank them, and extend an offer to the best one. If he/she rejects the offer, they will move to the next one, and so on. If you ever took a game theory course, or alternatively if you watched the movie 'A beautiful mind', you know this leads to a suboptimal outcome. Still, some companies like to do this because they believe the perfect candidate exists. That's life.

note 6: a bird in the hand πŸ₯š

Good news is: you will know which company you have landed on as soon as your interview cycle ends. If you instantly get a rejection, you've been lucky to find an 'early stop' company. If you get an offer, it could have been either - still, congrats!

But what if it's been a week of radio silence? Then you most likely have stumbled upon a 'fairest of them all' company. My tip in this case is to ask yourself the question: "Do I really want to work for a company that extended an offer to three other candidates that were better than me, and they all refused?"

My personal tip is that there is wisdom in the crowd: if you've finished the process, and there's been no offer in a couple of days, assume you didn't get the job and focus on other opportunities. After all, a bird in the hand is better than two eggs in the bush.

In my personal experience, companies that are good know the 'early stopping' is the optimal configuration as well. They know the perfect candidate doesn't exist, and value speed and fairness and teamwork over finding the one spectacular individual contributor. My advice here is: go for companies that give you a yes or a no fast, not for the ones that leave you hanging.

note 7: always, always, always negotiate.

Here's how your job offer looks on the hiring side. HR, the startup's CEO, or whatever other decision-making entity gives your hiring manager two numbers: a low one, and a high one. As long as your compensation package lands in the middle, the hiring manager can hire you with no questions asked.

In some places, the situation is complicated by the fact the team has a 'total budget', or stock allocations, or levels, but let's not get into that.

Now, if your hiring manager has decided to hire you, he or she will give you a number that is somewhere between the 'low' and the 'high' number. Regardless of the number, I recommend you always, always, always negotiate. Negotiating is hard and unpleasant, and your brain will make up excuses. Here's some common buts:

  • πŸ“£ "But the guys over at Company X have been so nice throughout the process, I don't want to make them angry". I can guarantee you no one will get angry if you try to negotiate. You're getting a job, not trading PokΓ©mon cards during recess.
  • πŸ“£ "But I don't have any other offer and if I negotiate they will rescind the offer". This will never happen. Never. The company has spent a lot of money and time to get you to this point. Worst that can happen, they tell you there's no room for negotiations and you either take the offer or go. This is usually a very strong red flag (remember the low and high number?), and you should go look for other opportunities.
  • πŸ“£ "But this offer is great, it's much more than what I currently make". Congrats, you were underpaid before and now you can continue to be underpaid for the next few years.

There's a lot more buts, but I think you get the drill. There is absolutely no incentive for your hiring manager to give you the best offer (i.e. the 'high' number); and I say this as someone who's always lobbied for fair salaries for new hires. The midrange salary is the fair salary.

Here's why: not all candidates negotiate, but the ones that do will be disappointed when they hear they're already at the top of the scale and you have no room for increases. So (good) companies will give everyone the midrange offer, bump it up for those who negotiate, save money on those who don't. Guess what you should do? Always negotiate.

⚠️ One last addendum for all HRs and hiring managers out there wondering why they should offer the midrange number and not the low number. "Surely" goes the HR in the back, "we can have even more negotiating range if we give candidates the 'low' number and take it up from here?" Well, here's the rub: assuming your high and low numbers are benchmarked on what the market is paying, a good candidate will get multiple offers - most of which are midranges. By offering the 'low' number, you will make it really easy for good candidates to reject your submarket, lowball offer, and end up hiring subpar candidates that are willing to take the L.

The optimal path is 'midrange offer, candidate negotiates' - can't argue with the Nash Equilibrium baby.

Note 8, 9: hostage negotiations

Ok, so you've landed an offer with a role you'd like and you want to negotiate.

This is a pivotal point. You probably are still interviewing with some other companies that you liked. And of course the company still has other candidates in the pipeline for your position, and is waiting for your refusal to extend them an offer. For the first time in the whole process it feels as if you, the candidate, have the upper hand. That feeling is entirely incorrect: you have an offer, not a contract. It's not over yet.

Note 8: getting the contract

This is how I negotiate:

  1. I write an e-mail to the HR person and the hiring manager directly, pointing out the parts of the offer I don't feel work out for me, and what it would take (= a number suggestion) to make them work. Needless to say, this suggestion should be realistic, but also leave some room for the company to negotiate down. In the same e-mail I ask to schedule a call to go over these points in the next couple of days.
  2. HR and the hiring manager look at my suggestion, at the original 'high' number they provided, and (if the company is good), what everyone else in the team / at that level is earning. We set up a face to face call.
  3. The company presents a revised offer. This is where market research and professionalism come in handy. No one wants the negotiation to blow up, so if there is any disagreements during the call, you are probably better off taking these points offline with another e-mail/call round. But if you were realistic about your requests, one round should be enough and you can conclude this whole thing in a day or two.

As soon as you get the contract, sign it. Done!

Note 9: not getting the contract

Not all offers lead to a contract. The 'I am willing to walk away' mindset is a luxury these days, for sure, but there are still some red flags you should watch out for, both in companies as in candidates. If you see one of these during the negotiation (from either side), I strongly recommend you go for another opportunity wherever possible.

Company red flags:

  • 🀑🚩 The company claims they cannot negotiate or change your offer because "it would not be fair to your colleagues, everyone here is paid the same".

This can be either a truth or a red flag, and there is only one way to know: ask HR for the 'low' and the 'high' number, and run it with your prospective colleagues. See if their stories and numbers line up with what HR is saying. If you're not feeling that brave, you can always look at Payscale, Blind or Glassdoor, but asking prospective colleagues is a surefire way to know. Companies where salaries aren't widely shared and discussed are the companies where the internal delta in compensation is the biggest. And yes, if HR was lying, asking this question will no doubt blow up the offer. But trust me, you don't want to work at this type of companies.

⚠️ For HR and hiring managers: as a general rule of thumb, I've found the 'colleagues' excuse is only used to shame you into taking a bad deal. Don't be that person...

  • 🀑🚩 The company claims your role is not defined, "join us and we'll find something to do"

It's absolutely OK to not know what role you'll be doing exactly when you apply. After your interviews, the company will have a good idea of where you fit in, and you will know enough about the company to suggest potential opportunities based on your experience and personal goals.

But by the time you get to offer negotiation, you should have a clearly defined view of your title, your role, and maybe even your first projects. Companies ask you "why do you want to work for us?". During the offer negotiation part you should ask "why do you want to hire me?". If the company does not have a clear answer, chances are either the company is bad, your role is bad, your team is bad, or all of the above. Do not take this offer.

  • 🀑🚩 The company claims your view of market rate salaries is skewed (of course, in your favour - no company will ever complain if you ask too low a number). They claim the salary and bonuses they offered are market rate and you should take it.

This is a tricky one, especially since "market rate" is such a loosely defined concept. In the end, companies are free to offer you whichever salary they want. Up to you to decide whether you want to take it or not - especially in case you like or need this job. Try to also think about the learning opportunities and future growth the job will offer you 1, 3, 5, 10, 20 years down the line.

Applicant red flags:

  • 🀑🚩 Nice guy/girl applicant turns into total a****le during negotiation.

Yeah, this is a toxic employee. Nice people sometimes turn into a****les, but a****les will never turn into nice people. And no a****le is worth the cost to the team - no matter how brilliant. Do not hire.

  • 🀑🚩 Applicant is very responsive during the process, but starts stalling as soon as the offer is drafted

Remember note #6? It's better to have a good candidate today than a million great candidates tomorrow. If the candidate wants your job, he or she will be eager to sign. A day or two of 'thinking about it' are fine - after all, this is a big choice. Anything after that means the guy or girl is waiting for a better offer from another company. As much as I hate the concept, I believe exploding offers do cut out candidates that were not invested in the job in the first place. If the applicant is taking his time to sign and negotiate the offer, a competent HR/hiring manager should understand what this means and either give the candidate a (short) timer, or blow up the offer altogether.

  • 🀑🚩 Applicant has unrealistic comp or job expectations

A very short one. Sometimes the candidate will be adamant they are worth X, and X is so far off to the right of the 'high' salary bracket, there is no way you can afford this guy or girl. The best option is to be totally upfront and transparent with the candidate: "we cannot afford this salary for your position". Usually that's where you part ways, and that's OK.

⚠️ Good HR will catch wild expectations before putting the candidate through the interview process. Also, good HR should probably communicate the candidate's expectations clearly to the hiring team - lest the negotiation step becomes a tense process in which both parties feel ambushed.

Note 10: good luck and a recap

To finish up: there is more to a life than your job, and there is more to jobs than the job hunt itself. Work is such a big part of our life: you will spend about half of your waking hours at work for the next few decades! My hope is you can find something you truly enjoy doing, that also allow you to put bread on the table for yourself and for the people you love. I hope these tips are useful for you: I sure would have loved reading them instead of all the bulls**t feel good work articles the internet is full of.

So, to recap, here's the ten commandments of the job seeker:

  1. ⛩️ Skip the great HR filter: try to get a referral where possible
  2. βœ… Fix yo' CV and motivation: quality over quantity
  3. 🎯 Stick the landing: understand what the company needs at the start of the process, and iterate on that!
  4. πŸ”₯ Ask hard questions. Make sure you can answer them: preparation pays off.
  5. πŸ“ž Talk to the president: make sure you speak with the right people during the hiring process.
  6. πŸ₯š If you like the company, take the offer! Don't stop thinking about 'two eggs in the bush'
  7. βš–οΈ Always negotiate: it's the optimal strategy
  8. β›³ Now get that contract...
  9. 🚩...unless you see obvious red flags. In that case, walk away if you can
  10. Good luck! May you find the job you deserve! πŸ€