Platform rewrites, part Deux

The last post was about what to avoid, this post is about what you can do to make a migration successful.

Sequencing is key

With any large initiative, the natural impulse is to throw a lot of people at it. Avoid this impulse at all costs. At the beginning of the project, it is better to have a small team of your crack developers and senior engineers and PM’s to focus on building a skeleton of what the end state would be like.

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Platform rewrites, lessons learned

At some point in your product career, you will do a systems migration or a system rewrite. In this two-part series, let’s explore some lessons learned. This first post is about the things to avoid before starting a systems migration. The second post will walk through some practical tips for organizations on the most efficient way to pull this off.

To set the stage – How do you get to the point of needing a rewrite in the first place? The general arc of startups starts with an MVP that is designed quickly. It’s all lean in the beginning, this is the MVP phase. Most backend processes are manual. It makes sense –  you don’t know if there is product-market fit and so you don’t over-engineer and make a full end to end software solution. As you find product-market fit, your user base starts growing exponentially and you enter the bolt-on phase. There isn’t enough time to slow down and add incremental features to the core product to make scaling easier. So you start bolting on hacks on top of hacks, pseudo automation based on excel macros and more policies and procedures to keep up with the growth. Your software system now gets to spaghetti level status.Read More »

Great PMs deal with ambiguity

I’ve always been interested in figuring out what signifies greatness in PM, what makes a great PM?

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A source of signal for me has been the ability to deal with ambiguity. Great PMs have this innate ability to take ambiguous thoughts/ideas/strategies as input and come up with a coherent executable plan which then they execute ruthlessly. A great PM has the superpower of bringing clarity to everything.

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Specialists vs Generalists – it’s nuanced and why you should read 10-k’s in your spare time

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The topic of generalists vs specialists always comes up in PM hiring and strategy conversations. I see PM hiring managers and PM’s themselves struggle with this a lot. What got me thinking about this topic is David Epstein’s new book Range. The core thesis in the book is, and I quote, “Range explains how to maintain the benefits of breadth, diverse experience, interdisciplinary thinking, and delayed concentration in a world that increasingly incentivizes, even demands, hyperspecialization.” So how should you think about this topic? What are the nuances?

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Anti Pattern – The Head Of problem.

The anti-pattern I’d like to explore today is what I affectionally call the head of problem aka senior’itis. In my experience, this is the factor in org design that increases burn and bureaucracy. This anti-pattern is lethal for companies.

It starts off quite innocently. Let’s assume you are the CEO at the early stages of a company and you have identified a problem to solve, say in the general area of customer support. Customer support as a function doesn’t exist yet. You ask around your peer group, you look at successful companies and then you make the common mistake – you get afflicted by senior’itis. You decide that you need somebody senior to run that function, you need somebody who has done it before somebody with pedigree. You need a Head of customer support. You then spend a lot of time trying to woo the right candidate, the one that checks all the boxes. You hire him after a long drawn out courtship. You are happy, your customer support problem will be solved, you have found the right person. You have hired a person who will take accountability to solve the problem.

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Nostalgia kills | Practical tips for leaders

Nothing is more responsible for the good old days than a bad memory – Franklin Pierce Adams

We’ve all read about how culture eats strategy for lunch. The internet is jam-packed with a million blog posts on the superficialities of culture. Its time for some inside baseball with some actual actionable things to watch out for and prevent.

It is absolutely true that the culture of the company dictates how it can adapt to change and eventually succeed. Culture is hugely important, however along the journey from a small company to a midsize company to a large public company, the culture will change. At all these stages, different parts of the company will have different cultures and norms. In fact sometimes within the same team, you will have differences based on where the teams are located and their size.

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Results don’t matter | Tips for better decision quality

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I just finished reading the book Thinking in bets by Annie Duke. I highly recommend this book if you want to understand how to make better decisions. She talks about this amazing concept called resulting that blew my mind. In her own words

…was a victim of our tendency to equate the quality of a decision with the quality of its outcome. Poker players have a word for this: “resulting.” When I started playing poker, more experienced players warned me about the dangers of resulting, cautioning me to resist the temptation to change my strategy just because a few hands didn’t turn out well in the short run.

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Idea killers, how to bounce back

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A key skill in my opinion as a product person is to identify “idea de-railers”. Idea de-railers are specific phrases used to block ideas from going further. Once you can identify this pattern, it’s much easier to plan around it, and as leaders attack it head-on. Below follow some choice de-railers from my collection.

Obvious disclaimer, Yes product managers should be empathetic, yes everybody in the company is driving towards the same thing so idea-derailers seems a bit harsh of a characterization, yes this is not ideal company culture, yes yes yes. However, reality is an approximation of the ideal, it always helps to understand human behavior (good and bad) and have a plan to tackle. These are just techniques that have been useful to me 🙂 Read More »