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Becoming Danny Ocean: tips for Software Engineers on Product Manager career path

Becoming Danny Ocean: tips for Software Engineers on Product Manager career path

Danny Ocean : “First task: Reconnaissance I want to know everything that’s going on in all three casinos, the rotation of the dealers, the path of every cash cart, I want to know about everything about every guard and every watcher, anyone with a security pass, I want to know where they’re from, what their nicknames are, how they take their coffee, most of all, I want you guys to know these casinos, theirs built to keep people in, I want you guys to know the quick routes out, third task surveillance: Casino security has an eye and ear on everyone, so we want an eye and ear on them.” — from the Ocean’s Eleven movie.

In 2014, after investing two decades into software architecting, I decided to continue my career as a Product Manager (PM). For some people, it may sound logical and for some impossible but technically it is like Livingston Dell (the electronics expert in Ocean’s 11) deciding for a “Dell’s Eleven” movie. It could have been more comfortable for me if it would be just one product and one team, but this wasn’t a startup; it was Yahoo. At any given time a PM at Yahoo balances time, requirements, cost, and quality of at least 5–7 projects, 3–5 experiments, 5–7 cross-functional teams, with daily releases, weekly sprints, monthly milestones, and quarterly measurable corporate goals. It’s like Danny Ocean running three heists at the same time, every month.

I’ve met many software engineers (SE) who are curious to become a product manager and want to learn more about the transition, challenges and are looking for answers. After providing suggestions in private conversations, I thought this could be a good topic which every software engineer can benefit from regardless if you are on a PM career path or not.

The big question: Why did you switch from SE to PM?

This question is almost always the first question I’m getting whenever I talk to somebody about my career, and the answer is straightforward and starts with the fundamental responsibilities. An SE is an expert on the “WHAT?” and a PM is an expert on the “WHY?”. So, the reason one switches from SE to PM is when you start becoming interested in the “WHY” more than you are interested in the “WHAT.”

Tip 1: Change your perspective from “What” to “Why.”

Changing your perspective is maybe the hardest and ever developing trait you need to work on. You need to unlearn the tendency, the inclination, the addiction to try to solve any problem you hear. But, this is harder than it sounds, because we software engineers are problem solvers; there is no problem on earth we cannot solve (or at least we feel like that) and it is our habit to jump on a solution. Coupled with strong confirmation bias (, it becomes a prison.

Having an awareness of this situation is the key to start the transition, otherwise “You can’t escape from prison if you don’t know you’re in one.” Therefore, you first assess your habits and accept the situation and work on your perspective. Until when? Until you don’t have any temptation to propose a solution when you hear about a problem (the “How”), but start asking questions (the “Why”).

Simon Sinek has a great TED talk, which explains the difference between “why”, “how” and “what” in ten minutes. And, I think this is the best place to start changing your perspective from “What” to “Why.”

Tip 2: Don’t have a manager, have a mentor manager

Even if you read all the PM books, take all PM MOOC’s it is almost impossible to organize the knowledge and shape it for the specific company, industry, team, and products you are managing. During your transition, it is essential to have a mentor who has already experienced in the company. It couldn’t have been that easy for me if I didn’t have a mentor manager.

Tip 3: Start odd small businesses

It sounds weird but, you need to know how a business works, period. I see a product manager as the delegate of the CEO in mid and large-size businesses. And, the experience of running a business helps you understand the different business aspects and the balances between them.

Luckily, there is a perfect school for this: the real business world. There is no better school, book or course other than the business jungle itself, and it is the fastest way to experience as many lessons (some name it failures) as possible in the shortest period. Most people maybe don’t know, but besides my three technology initiatives, I started a t-shirt business, a meditation app business, a chatbot business, a cosmetics business, and an online media business. The broader you venture, the more you start understanding the standard and core business aspects, like customers, marketing, sales, partnerships, cost structures, requirements, revenue models, forecasts, goals and more. I’m curious to hear what your unique business experiences and learnings will be. Please feel free to share in the comments.

Below are a couple of techniques and methodologies I would suggest which would help you with your business experiments:

1) Study and apply the Business Model Canvas (

2) Study and use GV Design Sprint (

Tip 4: Learn from the pros

The following books helped me with changing my perspective, and I hope you will find them helpful:

1) Sprint: How to Solve Big Problems and Test New Ideas in Just Five Days

2) How Google Works

3) Decode and Conquer: Answers to Product Management Interviews

4) Value Proposition Design: How to Create Products and Services Customers Want

5) Crossing the Chasm, 3rd Edition: Marketing and Selling Disruptive Products to Mainstream Customers

Tip 5: Cut off

“Decision” in Latin means literally “to cut off.”. You are either “in,” or you are “out”; make your decision to become a PM or not. I’ve heard many software engineers’ saying that they want to “try-out” the Product Management role part-time, but the reality is that the SE and PM hats are very different and it is not easy to switch them. Especially when you are building an image of a product manager in the company it is critical to have consistent core product management values. Therefore, my suggestion is for those who are on this route to make a decision and never look back.

Tip 6: Follow the circles

Circles is a method outlined in the Decode and Conquer: Answers to Product Management Interviews book for design questions, and I think it also forms an excellent framework for software engineers to follow during their work. It goes like this:

  • Comprehend the Situation

  • Identify the Customer

  • Report the Customer’s Needs

  • Cut, Through Prioritization

  • List Solutions

  • Evaluate Trade-offs

  • Summarize Your Recommendation

Lastly, congratulations on your decision to follow the product manager career path. It is an outstanding field that continually forces you to get out of your comfort zone and causes you to advance.

Of course, there is much more to say about the transition and many more subjects I did not mention. If you want to learn more about all the aspects of making the right decision, please check out my Stanford Continuing Studies course named "Product Management in the Artificial Intelligence Era" at Although nothing can replace a classroom experience, I'm also planning an online version as well for those who are not in this area.

Thank you for reading!

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