Lessons from my first Product Manager job

source: self-illustrated

First jobs are your entry point into the actual world. For me it opened a whole alternative world of startups, digital products, technology, and entrepreneurship, turning out to be a period of exponential professional and personal growth and absolute fun. As this year ends and so does my time at Shipsy, a Sequoia-backed startup, aiming to change the global trade landscape through tech, I have jotted down my lessons of the last 2.5 years.

These are not necessarily product management teachings (there are enough resources for that), but on ground lessons from my time at Shipsy. However obvious these may seem, every learning is based on my lived practical experience and observation.

Build systems, processes and workflows

• This seems too obvious to mention. But it wasn’t very obvious to me when I joined Shipsy. Life is pretty systemic till college — a timetable, fixed syllabus, exams time, evaluation criteria, bills being paid by parents in most cases. You literally are cruising through with no conscious thought.
• In large organizations, most systems are in place compared to an early stage startup, where everything is a blank slate. Whether it is communication, documentation, evaluation, delegation, YOU have to be the one to build these processes and structures.
• Find as many gaps as you can, to build processes and workflows, keep fine-tuning until the repetitive tasks happen in the most efficient way. Don’t expect things to be handed down to you. This not only helped me professionally, but I now try to find things in my personal life that I can build systems around.

Understanding ‘Working For’ v/s ‘Working With’

• As a PM, your team is not ‘working for you’, because you aren’t the one paying them. Which leaves the option of ‘working with you’. But they are engineers, designers, testers, etc, and skilled in these domains more than you. So why exactly should they work with you or listen to you? Further, how do they enjoy or look forward to it?
• It simply happens when they respect you and your judgement. This needs further breakdown. Respect can come in various ways. Domain knowledge, passion, logic, empathy, all invoke respect and connection.
• But not everything will work for you. I certainly couldn’t get respect from engineers for domain knowledge because I had none. So I started with empathy and logic and built up other weak areas. Put conscious effort into building traits to become a person, your team respects and is willing to listen to.

Be shameless in asking questions

• You can’t conjure products, services, or experiences in isolation. You are neither an all-knowing being nor can you read minds.
• I certainly struggled a lot here and asking for help didn’t come easy to me. Probably for the fear of being perceived as incompetent, which is a harmful mindset for growth. I can say with certainty now that risk being scolded, frowned upon, coming across as an idiot than not ask something and create fog in your own head.
• I am most grateful for all my tech teams who patiently answered my questions, explained the most complex topics and helped me understand system architecture and feasibility.

Devour the brain of your peers

• Learn how people think, understand their thinking pattern, discover who thinks on 1st principles, and then make them your friend or mentor.
• Be picky about people you spend your time with and be aggressive when it comes to learning. Peer learning is highly useful, next to self learning.
• I would often think of a solution and then ask my peers to also think upon the same problem and figure out if I missed touching upon some points and traced back my thinking structure. To the people I did this, I am really thankful and also sorry (not sorry)!

There are jewels to be found on a risky path

• Again, it might seem obvious, but the world makes you think that you first somehow need to be magically good at something and then pursue it. But you only have to know there is a viable opportunity and then pursue it relentlessly.
• When we entered global trade and shipping, it was an absolutely unknown forest. I remember when the most basic industry fact seemed like a big insight because everything was new learning. Cut forward to today, where Shipsy got selected for Sequoia’s prestigious Surge program with 6 million funding to build an entire end to end product for shipment management for global trade!
• It wasn’t because the founders could foresee assured results, but because there were single-minded efforts to achieve the vision of revolutionizing the industry. You don’t pick up something because you are good at it; you do things and then become good at it.

Not all forms of communication are useful

• You’ll spend a lot of time communicating with every team. Communication is the key and your time is the lock. Avoid one-to-one calls or chats as much as you can. Calls may seem like a quick way but go for quick team meetings, catchups, messages on groups.
• Yes, sounds simple, pretty basic stuff but will save a ton of time and energy, usually spent in bringing everyone on the same page. Don’t be afraid of things going wrong, be more afraid of not communicating it on the right time.

Find questions not answers

• Being completely dwelled in a problem is necessary. Brainstorming, which I think is a weird word, is super important. But you can't brainstorm alone and come up with solutions, though. The good news is that you aren’t supposed to. The first aim is only to come up with the right questions.
• You don’t have to have all the answers. Answers come from various sources: peers, seniors, the internet, industry experts, and mostly your users. Answers aren’t the hard part, the questions are.

It is not enough just to create

• The product tech space is great for people who don’t want to follow fixed paths and pick up skills from each arena, be it sales, tech, business, design, marketing, consulting.
• At the end of the day, it is just product thinking that one needs to develop. An answer to the questions — how to identify an idea/ gap and how to make a product/feature out of it for which users pay? The above question encompasses everything from why build something to who will use and pay and how to scale it?
• So essentially you need to have a maker + salesperson attitude to be a PM. One without the other won’t take you very far. It is something that I too have been trying to get my head around.

Craziness is good, blindness is deadly

• You need to be a little crazy to build a company. With all due respect, I think the founders of Shipsy are absolutely crazy. Anyone who is so obsessed as them has to have a loose bolt in the head, but then, it is the loose bolts that really create something.
• I think using the craziness to your benefit means to attach and detach yourself from situations. It is basically the art of having a first-person view and immersing oneself completely to not be distracted and also being able to see the situation from a third-person view, completely detached, to measure, halt or pivot. Almost like having both the bird’s and the worm’s eye view.
• It is nothing but a mental model, something I am yet to imbibe. A lot of things needed to be abandoned at the optimum time at Shipsy for the next right thing to start. If you are too blind and narrow-sighted, you’ll miss the big picture altogether.

Don’t try to do everything yourself

• Find the right people if you wish to be in the entrepreneurial world. It might take time, but is absolutely critical. You’ll spend a significant time building something with your co-creator or team, maybe more than your family as well.
• So don’t try to do everything yourself. Consciously find people with complementary skills not overlapping or similar. Our 4 co-founders, strategy officer and advisor, fill up complementary skillset, making the complete unit a solid one!

Hire beyond the basic requirement of doing the job well

• Do not underestimate traits like empathy, ownership, and hunger to learn. People can be trained in skills, but not in empathy and rarely in ownership. Envisioning the culture and then finding the right culture-fits to cultivate it, is what takes the organization forward. Shipsy is a massive example of that. Employees will join for various reasons, but culture is what makes them stick.
• Find trainable people but give them the benefit of doubt if they show natural ownership, eagerness to learn or leadership attitude. I clearly remember when I was interviewing for a designer, the person I hired was only because he seemed to have immense ownership attitude and is now a critical member of the design team. There are more examples where Shipsy gave people with such traits, a chance to start with and they have been instrumental and inspiring.

Find a connection with the problem your product solves

• This is purely a personal newly picked up mental model I want to test. Try to find out if you connect with what you are creating and if the problem makes you feel excited and relevant enough to dedicate yourself to it.
• I have not found out the answer to whether a PM should be emotionally connected to the product they create or just focus on the process or be agnostic altogether.
• This is not a pre-requisite or a deterrent for success. Product thinking and learning should be repeatable, and one should be able to call upon their frameworks when creating, not necessarily their emotional investment and connection. But the question is definitely worth asking yourself.

Create your own little ways of working

• As a PM, make your own documentation style, develop personal frameworks of thinking and researching, keep your notes and sources from where you learned something, follow industry news and veterans, without getting bogged down with cognitive overload, that is.
• I definitely lacked in the documentation department initially. Even rough drafts of ideas are important. It is okay to publish initial thoughts for discussion.
• Write down meeting notes without fail as you are bound to forget a lot of things. There are amazing tools like Paper, Notion, Evernote, Notes app in mac. Find if you like writing digitally or pen and paper. I personally need to have a notepad at all times.

Action-oriented talking

• Make sure whatever you are saying can be linked to an action, especially when communicating with higher management, who probably are handling way more than you are. I specifically learned this from one of my co-founders. This way you won’t end up blabbering.
• This not only helps you become a more logical and structured PM, but also makes you decide which thought to pursue out of a hundred thoughts that strike you. If what you said has no actionable insight, it probably was a waste of time.
• So from ‘We shouldn’t have done this’, move to ‘X went wrong, so we need to try/change Y’. This sounds small, but it had a big mindset change for me personally. I have been able to keep my head clearer, saved time, and discarded a lot of useless thoughts that have no further actions.

Ideal solutions are deceptive

• If you work in the tech industry, chances are you are a logical, structured and analytical person. Obvious ideal solutions may seem the way to go.
• But there are always more constraints than just building the ideal solution. Always keep in mind constraints like bandwidth, feasibility, time, effort vs value, scalability etc. The most obvious ideal solution is rarely the most pragmatic approach. You may end up going with a second or third proposed solution, and that is perfectly fine. There isn’t exactly anything called perfect because you’ll always be iterating using new feedback.

Only measurable growth counts

• We are all growing, learning and changing at all times. And growth can be an extremely complex and intangible concept. Like, you controlling your anger better is also a big growth point. You’ve managed to become better at both your work and teamwork.
• As harsh as it may sound, personal growth and learnings are a waste, if they can’t be applied and used to generate a desired outcome and value. It is possible only when we define metrics to measure that growth. It goes back to building systems and processes around measuring

Auto-Pilot Mode is a scary place

• Lastly, know the difference between active learning, passive learning, and floating around in auto-pilot mode.
• It is not uncommon for PMs to question what exactly are they doing when they work in an early stage startup. For example, situations where you might need to stay back late for a release, even though there is nothing for you to do, is an exceptional situation of learning. It helps you answer:
• Why exactly are we staying late? Is it a delay or a working style? Do I need to babysit my team or train/ find people with ownership? Do I like my team enough to maybe not mind this situation? Does it imply dedication for a timeline or poor planning/ execution? What part can I play in such situations?
• Any situation where you even learn about yourself as a person or lets say learn some internal intangible skill like confidence, grit, teamwork or even discovering that you don’t like something, is absolutely valuable even though it is passive learning.
• What is harmful is not learning from situations, active or passive. Living in auto-pilot mode without questioning and not caring enough about your work. That I am personally scared of and you should be too!