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Breaking into Product: What I wish I knew

. 10 min read .

A  guide of the DOs and DONT’s of landing a product role all the way from the application to the interview stage + a list of the top 50+ questions I got during my hunt.

For the past 3 months, I have been focusing on one thing; landing a job in product. Do I know what I am talking about because I got 10s of 6-digit offers? On the contrary, it went through 64 rejections. 64 hard falls after which I tweaked my process and came closer and closer to that dream role.

You can read more about how that went in Part 1 (6 minute read) and checkout a snapshop of my background through my CV. But for now, here’s what I wish I knew from the get go.

I. The (Bitter) Truths — Managing Expectations

  • Product is still underdeveloped in Europe. The majority of the positions available are in the States (65% in my case) vs whole of Europe. This means less product roles of course and even less entry level product jobs (which are rare either way).
  • People rarely get VISA’s to work in other places (USA) unless they are very skilled (years of experience or outstanding university and qualifications) or there is a big shortage for that role (ex.developers). This means that entry level jobs that need a VISA are pretty hard to getfor obvious reasons. Try starting from a company that doesnt need a work VISA and transition to other countries in later stages of your career. That doesnt mean don’t apply to them! I was lucky to get 3 interviews. Just don’t put all your stakes there.
  • Early stage companies probably do not have the resources to sponsor any VISAs or hire junior PMs. This means that you will rarely find such roles in very young startups. Funded, more mature and bigger companies is what you are better off looking into.
  • Companies just don’t hire many graduates because they are just expensive. They don’t have much to offer and need significant investment to train and mold. That’s why the hardest part of your career is the beginning if you ask me. So it is ok not to start from your dream company or dream role. You can transition to that anytime later much easier.
  • Companies hire very few graduate PMs. PMs is one of those roles that simply goes hand in hand with experience. The value of junior product managers is hard to justify and it is something that is not as ‘essential’ as developers, marketers, HR etc. If you find it too hard, don’t give up on product. Consider starting as an analyst or on another department where you can get in ‘easier’ due to your current skills and internally transition to product. You just need to ‘sacrifice’ some things at the beginning.
  • Product roles are limited and in demand which makes them VERY competitive. Just think that, on average, for every product manager in a company there are at least 5 to 30 developers (depending on the company ofcourse). Product roles -and especially junior ones- are by no stretch of imagination in abundance.
  • At the beginning we all suck. The more you do the interview thing, the more relaxed you will be, the more confortable you will look and the more spot-on your answers will be. This is just natural but keep it in mind.
  • Don’t be deceived nor disappointed by all the success stories. Don’t put your chances in these hard to get APM roles like Google, Twitter and Facebook because we are talking about a super limited number of places.No matter how many success stories we read we NEVER read about the 100:1 failiures who do not put their stories online.
  • Yes, it is tough but it is worth it!

It has been tough for me to realise these things the hard way, through rejection after rejection. A lot of reality checks along the way. But I think it is important to know these things so that you manage your expectations and ESPECIALLY not think you suck and you are not meant to be in product! It is not you. It is just the nature of the job, the state of the industry and capitalism. =P

II. Tips & Advice

Ok so the hard part is over! Let’s get into the fun part!
The usual disclaimer: I am not an expert recruiter. This is just my perspective.
Also note that I did NOT do all of this(i.e. they are not essential); but looking back, I wish I did.

1. Before you apply

  • Read read read. Medium articles, Newsletters, books about product,management, tech, specific industries etc. It teaches you how to talk the product language and can spark conversations during the interview.
  • Side projects are gold. If you dont have any, consider starting some. A mobile app, a website designed from scratch, a blog(see below) etc.They add some variety and richness to your application, show them that this is your life not just your job and ofcourse show your practical abilities > just words on paper.
  • Consider starting a blog. Write about stuff you love not necessarily career. Maybe do some product critiques or redesigns. Even if you have 0 readers it will help you for sure and add some personality to your application.
  • Join online product communities: Become member of the Product manger HQ, Product Tribes & Mind the product Slack groups. Also Product Managers’ Community in FB. Contribute, ask questions and ask if anybody has any role to suggest.
  • Network. The best roles out there are not even advertised or are waiting to be created ;). Still regret not doing enough of this. >_<

2. Seeking

  • Use aggregators & setup alerts. My favourites are betalist, Angellist, LinkedIn, & mindtheproduct and don’t forget to setup alerts. Not all jobs are listed in aggregators though. Try the Slack and FB groups mentioned.
Jobs I found per source and time invested searching in order to find each suitable job post (taken from Part 1 of ‘Breaking into product’)
  • Apply everywhere! Don’t be very very picky. The statistics speak for themselves. You will sometimes be pleasantly surprised (I often was).
  • Even if barely eligible; apply! Job descriptions are written for their dream candidate and companies know they probably wont find that.
  • Leverage your uniqueness: Find companies where your unique background can give you an edge. For me, for example, would be aerospace, engineering, drones, fintech & blockchain companies.
  • Send your application in ASAP. Most roles are filled and pulled down as soon as the right candidate is found. Thats why you dont see a ‘closing date’. They dont wait until X date and then choose between candidates. If they find the person they want, the job posting goes down.

3. Applications

Applicable to resume, Cover Letters(CL) & Interviews

  • Be yourself. You probably hear it all the time: Be authentic. Recruiters know that if you are happy and fulfilled in the role then you will perform the best. They also understand that you have to fit the culture. Not for their own good but for yours as well. It is a give-take. If you were truthful during the whole process and they rejected you, trust me, they are doing you a favour!
  • Find your superpower(s): What is it that distinguishes you from the rest? Maybe your electronic engineering background, your ability to handle data very well, your experience in marketing, you specility in e-comm. Product managers are jacks-of-all-trades but it would be great if one had that T shaped skillset.
The T-shaped individual. Made popular by IDEO’s Tim Brown. Artwork by Zhiyong Li’s “Lost Hometown”. Typeface: Luna by Amanda Leeson.
  • Always seek to differentate yourself. Explicitly state what makes you different. This makes you memorable. It might be your ‘superpower’ mentioned above, a skill like machine learning, a hobby like freediving, backpacking around Asia for a year and so on. You can also differentiate yourself with a unique resume design, a portfolio attachment, a reference or a special research project done for them(see below).
  • Show them! If you are really passionate about the job, do a pre-application project for them. That could be a usability test, user research, a data analysis task, a new feature design etc. I spent 2 hours doing this for example(pass:yelpme!).
  • Recruiters are busy people. They won’t spend much time on your application so keep it short and to the point. No fluff. Clean and concise.
  • Get in their head. Use empathy to understand what they want to hearand how they would interpret your application and background. Then tweak them accordingly.
  • Talk from a position of power. Don’t sound desparate(even if you are).Don’t sound miserable. They need you as well, not only you them.
  • Don’t put yourself down. Be honest about your weaknesses but no need to emphasise them yourself. Be sure, they will ask you themselves.
  • Your value. It should be loud and clear how there is fit and how you can provide value both in the CL & Interview
  • Use storytelling in CL & interviews. It makes it interesting and engaging.
  • Reach out to real people. Don’t just send in an online application. Contact them on LinkedIn. Why not a chat over coffee? Nothing to lose.


  • Quantify and add some meaningful detail to what you did. Don’t keep it too vague and high level. For example: used <tool/procedure/method> to <activity> and I achived <result or metric of success>.
  • Be laconic. Not in terms of useful content but in terms of expressing yourself. No need for fully composed sentences with rambunctious words.
  • Consider attaching references even if you are not asked for any.
No better way than to show you. Here’s mine.

Cover Letter

  • Don’t be too sleezy nor cheesy.
  • Don’t be too soft or emotional. Vulnerability is strength but not everybody perceives it as such, instead = weakness.
  • Don’t use many emojis🙅 🙅‍♂️. They often subconsciously hint incompetence, not friendliness.
  • Take some time to research and customise you CL. Specifically: Why you are the perfect fit for this role (look what they want to hear in the job description), why are they and their product exciting for you, do you have any thoughts about the future of their industry, what is something you would know only if you did your homework?
  • Make your cover letter customisable and scalable. You should need less than 15 minutes on each for each role. In my case, the first 4 paragraphs were my story which pretty much stayed the same and the last two paragraphs were to do the ‘customisation’ discussed above.
An example of my CL version 1923712 (still fighting to reduce its size)


  • Ask the recruiter about what you should expect. Who is the interview with, what will the nature be(technical, informal etc.), anything you have to prepare? etc.
  • Prepare the questions below out loud. Consider creating flash cards or ideally ask sombody to ask you. Remember to read the role description again and adjust your answer to what they wrote!
Product Interview Questions
GENERAL QUESTIONS How did you define your success in past roles? How would you define your success in this role? What are you looking out to get out of this role? What particularly interests you and would you like to learn from this role? What would be your dream role? How do you imagine a day...

Even more questions here.

  • Find Insights: Of course you have to know about the company, the role and the industry beforehand but try to find the latest news that only somebody who is really into them/the industry would know like their latest release or something state-of-the-art in their industry etc.
  • Don’t be late
  • Interact like you would everyday. Dress how you would at work.
  • Converse. The interviewer is not supposed to shoot at you and you dodging bullets. Ask questions back. Ask them about their opinion about X tool, their previous experiences or whatever you find to have in common.
  • Listen. No; truly do. Use stuff he/she said in some of your answers.
  • Smile, joke. They want to see you are plasant and chill to be around.
  • Put some thought into the video call. Choose a nice backdrop, check your connection and battery beforehand.
  • Do they look busy or distracted? Don’t let it get in your head. It is not you. They usually take notes digitally to forward to the hiring manager.
  • Practical Challenge: Be ready for a whiteboard design challenge.Prepare at least a strategy of how you would work. For example you might be asked why would you go about designing a mobile app for X.Your strategy might be: 1.define problem clearly, 2.define requirements and limitations, 3.construct a brand etc
  • Ask good knowledgable questions for them that show insight of the company, the role and the industry.
  • No bragging: Even if you have other offers, no need to rub it in their face. They will surely ask you themselves.
  • Read this awesome essay by Ken Norton on how to hire PMs.


  • Reach back if you don’t hear back. Thank them after an onsight interview. Tell them that after it you are even more excited (they do want to know if you did or not). You are not ‘annoying’, you are ‘interested’. Also don’t get hurt. Many companies just have that habit of not answering😒.
  • Do not burn bridges. When you get offered an opportunity that is not what you are looking for or have to reject an offer after accepting another, spend some time to get in touch and explain your decision. Never leave messages unanswered just because you ‘don’t need them anymore’.

All in all, the main focus with the whole process is to think of what they would like to hear and filter your response accordingly.

What they are trying to answer is very simple and twofold: Are they right for you? Are you right for them?

Hope this helped a bit.

Good luck!🙌