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⚡️Adam's Product Management Newsletter - Issue #5 - Product Roadmaps and the roadmapping mistakes I’ve made

Adam Wintle
Adam Wintle
Hi there,
Back in 2017 I was Head of Product at Time Doctor, a time tracking and employee attendance SaaS product.
The company was 100% remote, with over 80 people in 28 different countries (such as Poland, Canada, Thailand, Bulgaria, Indonesia, Australia, Egypt). Every year we held a whole company retreat in some exotic location, such as Miami or Bali.
In September 2017 about half the company met-up in Greece, Athens, which almost the entire product team. The CEO couldn’t make it so I played a pre-recorded message from him, and then I opened with my main presentation.
I wanted to kick-off the 5-day retreat with something special, something big and something memorable. We had people traveling from all over the world to the company meet-up to plan out the product for the next year and beyond so I really wanted to inspire everyone and help build momentum towards what I had envisioned for the product.
My opening presentation was “The 10 Year Roadmap for Time Doctor!”, a spectacular and visionary roadmap for the product. Many features such as machine learning enchanted predictive timesheets, Slack bots, Chrome Extensions and more…
What I realised is many people in the product team weren’t focused on these long-term goals. These were far-off outputs that we maybe could achieve.
Instead, everyone wanted to talk about potential problems which could be just around the corner. What did we want to achieve next? Where does the business and higher management see the product heading in the short to medium term?
I had made my product vision way too broad; my 1-3-5-10 year plan didn’t really mean much to my team.
After the company retreat I headed to the 2017 Mind the Product event in London. This was my first time at the main London conference and here I met someone called Janna Bastow, the CEO of ProdPad. I’d describe ProdPad as a “notepad for product managers to help communicate product things to everyone else”, it has roadmaps, plus a lot of other useful product-focused features.
When Janna demoed the roadmaps featured I realised I had made a grave mistake with my team in Greece.
I had gone for the long-term vision, the big grandiose vision of what the product could become.
What Janna introduced to me was this concept of an “outcome-based roadmap” plotted across a shorter timeframes of “now”, “next” and “future”.
This for me was some kind of sudden moment of clarity! This is the obvious way to do a product roadmap.
In early 2019 I left Time Doctor, and as far as I’m aware my 10-year roadmap is not underway. This proves to me I was way too forward-looking and way too ambitious with my product roadmap.
In the rest of this week’s newsletter, I want to share with you some articles I’ve found useful and helpful over the years. I’m now personally I huge advocate for the “outcome roadmap vs. the output roadmap”, and I encourage you to look into it.

How To Build A Product Roadmap Everyone Understands
What does an agile product roadmap look like?
Outcome-driven product roadmap
Escape From the Feature Roadmap to Outcome-driven Development
Outcome-based Product Roadmaps: a missing link in Agile Product Development
The Alternative to Roadmaps
Thank You
Thanks for sticking with me through to issue five of my newsletter.
I took a bit of a risk this week and went with a storytelling approach in my opening letter.
Let me know if you enjoyed the story or what your thoughts are on my situation back in 2017.
As always, if you enjoyed the newsletter then please share it with your friends and colleagues.
Thanks again,
Adam Wintle
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Adam Wintle
Adam Wintle @adamwintle

Focusing on People and Product: the intersection of psychology and product management.

After working in product for over a decade and speaking to many other product mangers (as well as UXers, growth people, marketers and techies) the number one struggle I heard again and again is that people are at the root of the majority of the problems.

Once you have mastered the basics of product management. Once you have read all the books. After you’ve been to all the conferences. You’ve seen all the YouTube videos; you’re a member of all the Slack communities. Then you are only left with learning how to lead, work with and manage other people, to get them all aligned and pointing in the same direction, so you can build your product vision and ultimately build a successful product.

This art of People & Product can take decades to master. I’m certainly not a master of this yet, but I thought you might enjoy following along on my journey. Want in?

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