5 Lessons from a Decade in Tech

As August 17th 2025 came and went, I wanted to take a moment and reflect on my first decade in tech and how it has shaped me in the Product Manager that I am today.

So in no particular order ( uncharacteristic for a PM I know), here are the 5 lessons that have shaped my view on the Product Management profession.

Getting in front of customers is hard

You know that feeling after you get off a customer call - that you have their problem fully understood and you are now armed with the insights that will change the entire course of where your company is headed. That might be an overstatement, but at the least you feel like you know what the next thing on your roadmap should be. It's those conversations with customers that fill my cup. It's the reason why I became a Product Manager. I wish I had that feeling all the time.

So why is it so hard to get in front of customers? There are thousands of reasons why that's the case, and I'm sure you're well versed in them. If I had to single out the biggest thorn in a PM's side it can be summed up as : "I don't talk to customers enough.".

So what can you do about it?

In my experience, the thing you need to change is to stop relying on other people to get you in front of customers. The same way an SDR is cold calling to get leads or an AE is following up to book the next meeting, you need to reach out to customers to get 1:1 time with them. Mine your Product or CRM for the account holder details and send out emails. Build an in product survey that links to your calendar so that they can book a time that fits their schedule. You can reach out in many ways, but the important thing is to build those direct relationships.

Thinking beyond 6 months feels impossible

Most PMs are busy writing PRDs, grooming their backlog and working the short-term roadmap. But if you ask them what they should be building a year from now, and they draw blanks. That's a problem. Staying in execution mode keeps you from building that strategic muscle. Maybe you don't have the time for it, or maybe it's because that strategic work is full of unknowns. Whatever the reason, this is a major barrier to growing into a leadership position.

I'm not going to give out the family recipe, but I will share one ingredient from the secret sauce. Make the following question a part of every task you're doing : "What will this be in 2-3 years from now?".

You could be working on an integration that allows you to bring in crucial HR information into your platform. How will this will change over then next few years? What innovation is happening in that space? Are there new incumbents and how are they differentiating themselves? It will undoubtedly be buried in your discovery doc and no one will read it. That's ok.

The important thing is that it will have stuck in your mind. Given you a new perspective and shaped the way you see the subject. Compound that week to week and it will give you an informed opinion about the questions on everyone's mind: "What should we do next?".

You can only build so much

Finite development resources are the great equalizer. As a PM you will often struggle with this rigid constraint and be tempted by the "feature factory" mindset. Believing that success is one feature away. What I once as a barrier to success, I have now come to embrace.

There are lots of factors that will influence how impactful a feature or part of a feature will be. Customer context, usage data, user testing, competitive analysis, etc. The one thing I ask myself time and time again is "Can problem X be solved without feature Y and will that allow the user to accomplish goal Z?"

It's a simple Yes and No question that when used correctly, can make prioritization much easier. It will allow you to fully own the constraints in which you are building and leverage them to maximize the outcomes you are looking for.

Another technique is to only write down the most important requirement I need to solve for. This allows me to go from a place where I need to prune down a feature to make it a reality, to having to add requirements to make it usable. And yes, your feature specific backlog will grow. You will need to explain why thing 1 isn't on the list and why thing 2 didn't make the cut. That's a much easier conversation to have when tangible value was delivered to the user. Constraints don’t weaken you as a PM. They sharpen your decision-making.

A/B testing is a pipedream

A/B testing should be thrown in the buzzword garbage can at this point. In start-ups or scale-ups, we don't have the luxury to build two versions of the same thing and see which one works best. I have done 1 true A/B test in product and it was a minor feature. The result pretty much confirmed our original hypothesis, but that's not the point I'm trying to make here.

A/B testing belongs in the design phase. Your designers are most certainly testing a lot more than two options. User testing is much cheaper and produces far better results.

What PMs should be focused on is actual testing. Shipping a feature that isn't fully baked, can still help validate if a problem is worth solving. Prove that solving it provides value. Getting a user to interact with something is much more important to finding where your product can be successful, than what that feature looks and feels like. Leave A/B testing behind and focus on testing; it's the sure way to know if you should kill it or scale it.

You live and die by your stakeholders

A great PM has an intrapreneurial spirit — building like a founder inside an established company. And the truth is: your success depends on how well you bring others along.

Get your internal stakeholders on board. From doing discovery and building your pitch, to getting UAGs from a dev lead, needless to say that you need to come prepared. Beyond that, having conversations at the right time with the right people will allow you to create allies.They will undoubtedly uncover things you didn't consider or implications that were unknown to you.

Putting the intrapreneurial mindset to work allows you to engage your internal stakeholders on forward looking initiatives that can move you product in the right direction. It's easy for a PM to fall in the blame game and forget that their greatest strength is to engage with the people inside of their company so that they can build products for the people outside of the company. That is impossible if you don't convince them that the problems you've identified will help grow the business and affect the bottom line. So be the voice of the customer and get your executives and senior leadership to rally around you; they are your greatest allies.

If you’ve made it this far — I hope one of these lessons sparks reflection or helps in your work.