Portfolio The Messy Middle: Finding Your Way Through the Hardest and Most Crucial Part of Any Bold Venture

I just finished reading The Messy Middle by Scott Belsky and highly recommend it for product managers at both startups and established tech firms. Scott Belsky shares his lessons learned optimizing and enduring the messy and unsexy middle every product goes through before (hopefully) thriving. He does a great job of sharing lessons from his own experience founding Behance and navigating Adobe post acquisition, as well from the many startups he has worked with as an investor or advisor, including Pinterest, Airbnb, Periscope, Square, and more.It's a difficult book to summarize because it's organized as 100+ mini-essays that succinctly teach a specific best practice around optimizing your team, your product, and yourself. But what I loved most was that Scott brought a far more human lens to creating winning products than traditional product best practices. I wanted to share 5 such non-obvious lessons that really stem from Scott's deep understanding of human behavior, human psychology, and human intuition.Nobody remembers, or is inspired by, anything that fits inWe often seek to describe what we are making in terms of what already exists, like the "Uber for massage" or the "Apple of razors" in an attempt to be relatable and easily understood. The downside of this is that we give up free-range innovation as the expectations for what we are building then become set by the analogy. Scott advises us not to succumb to society's gravitational force toward what is common and familiar because it can result in your fresh insights being pulled back to the mean of normalcy, thereby killing the uniqueness of the innovation you initially contemplated.Beware of creativity that compromises familiarityWhat's so interesting about The Messy Middle is that Scott fills the book with apparent contradictions, with one essay arguing for a specific best practice and then the next arguing the exact opposite. By doing so, Scott is sharing the real-world balance and trade-offs inherent in any tactic. This essay served as that exact foil to the above. In it, he suggests sometimes in our attempt to disrupt an industry, our instinct is to be different. But often the best way to capture share of an existing industry is actually to be familiar. He describes how the team behind the June smart oven originally designed a wildly different-looking product that re-imagined what an oven even looked like. But they ultimately realized that if they wanted it to be considered as an alternative to an oven, they were better served by a product that actually looked like an oven. Since they were already trying to disrupt cooking, going with a more familiar form ultimately aided their adoption. To reconcile this with the above, Scott gives us the following rule of thumb: the only time you should force new behaviors is when they enable a unique and important value in your product.Measure each feature by its own measureWe spend so much of our time building engagement drivers into products, features and experiences intended to drive customer engagement of some kind, based on our understanding of customer needs. But simply marketing our products via engagement drivers misses a key human insight: that customers don't always get most excited about the features they are most likely to use. Instead, the features that excite people most are often the novel features, even if they aren't necessarily practical. Scott calls these the interest drivers. He shares how HBO GO initially promoted it's offering with the launch of Game of Thrones by introducing a detailed map of the fictional geography into it's app as a way to encourage people to download the app on their iPad. Even though it ultimately wasn't a heavily used feature, it's novelty drove awareness and trial of the iPad app. It's important then to realize when you are building engagement drivers vs interest drivers and to hold each feature to the appropriate measures for what it is ultimately designed to drive.Mystery is the magic of engagementIn this essay Scott details the leading psychological theory on curiosity, known as the information-gap theory, describing how curiosity proceeds in two steps: 1) a situation reveals a painful gap in our knowledge (say a BuzzFeed headline), and then we feel an urge to fill that gap and ease that pain (and then we click the link). This behavior is so pervasive and is equal to other primal desires like hunger. Scott encourages us to take advantage of this when marketing our products. Instead of simply providing a tell-all about your product, the best marketing taps into the natural human tendency to want to learn and understand something that is not fully revealed. Unanswered questions drive intrigue, even if you weren't necessarily interested in the answer in the first place. Apple, with it's carefully orchestrated product launches and reveals, is the king of this, but all of us can take advantage of what Scott calls the "magic" of engagement.Data is only as good as its source, and doesn't replace intuitionWhile Scott shares lots of lessons throughout the book on how best to take advantage of data, in this essay he warns us that some of the best decisions you make may in fact run counter to what the data suggests and are instead driven by intuition.He shares a great case study at Square: a few years back, Square pioneered finger-based signatures in their cash register experience. Ultimately when VISA and Mastercard decided to no longer require signatures for transactions below $25, the obvious thing to do would have been to remove the signature experience from those transactions to significantly speed up the transaction process. But Square didn't actually do that, because they realized that people found the signature experience somewhat fun and it also was a key branding component for Square and often the only way that customers were introduced to the brand. Even to this day they allow merchants to turn off signatures for transactions below $25, but it's on by default. A great example of how a core product decision wasn't driven by what the data clearly suggested, but ultimately was a win for Square.I hope this gives you a taste of some of the insights Scott shares throughout the book. It's chock-full of so many more, so would encourage you to dig in yourself: The Messy Middle by Scott Belsky.

Most books touch the surface of what it takes to achieve high aspirational goals, but The Messy Middle by Scott Belsky gives a comprehensive insight into what it really takes to reach them and long-term success, covering the highs and lows of the journey built on seven years' of research.You read in books and the news new venture kickoffs with inspiring missions and the big celebratory achievements giving a sense it's quick and easy to reach them, whether it's funding, IPO, market-leader status, job role...when in reality it's not and instead takes relentless patience, grit and empathy to achieve long-term success which is the focus throughout the book.The book is structured well keeping to around two pages on each subject, where Scott gets right to the point and focuses on modern approaches to help build and optimise your team and improve yourself."Milestones that are directly correlated with progress are more effective motivators than anything else.""The only 'sustainable competitive advantage' in business is self-awareness.""Don't start to question your gut solely because it is different. Nothing should resonate more loudly than your own intuition. The truly differentiating factors of your project are the ones most likely to be different, misunderstood, or underestimated by everyone else.""Every leader needs to come up for air now and then. By temporarily disconnecting from your journey, you're able to take perspective of all the moving parts." - very relevant as I read this on holiday.A fantastic read which I'd recommend to anyone struggling to progress towards their missions, looking to make sense of their experiences or generally interested in learning from Scott's journey and wisdom.

The Messy Middle is a book of honest-to-goodness value written for founders; outlining customer/user experience tactics that work, business & revenue generation (the right way), and how to navigate the emotional rollercoaster of team ownership when you still 'aren't quite where you should be'. It's one of those books that tends to refocus you when you didn't think you had to refocus at all and brings you back down to earth when the tech universe tells you to forget logical business tactics and go raise millions in venture capital so you can do everything famous unicorns do -- so you can be one yourself one day. It doesn't work that way; it's a basic probability issue, really.Some handy features I liked about this piece include:- Short bursts of knowledge: enables you to digest and move on quickly- Patterned thinking: the author only uses 'jargon' if required with the purpose of outlining quick processes and juxtaposing positioning for instant conceptual consumption- Introverted perspectives: I'm an introverted founder myself, so advice like 'DYFJ' comes in handy pretty much... every day- Pride in slow and steady: there's a ton of obstacles and stress that hit you every single day as a founder so the additional pressure, added by the tech world and critics therein, is dissipated by a focused understanding of value and iteration.This is pretty much the best book I ever read for entrepreneurship so far and I look forward to his next work.

Every time I meet someone who read this book and I ask them about it, their face lights up and they rave about it. Seriously, people get really passionate about this book. After reading it now twice, let me join in: I can’t recommend this book enough for anyone starting an organization, building a product or service, leading a team, or seeing through a big long-term project. It has amazing insights about hiring, managing, and motivating people for almost any context, plus many nuggets of wisdom on branding, selling, negotiating, and UX design, as well as sage counsel on self-management.As we know, it’s easy to come up with ideas and get excited about starting something. Scott helps illustrate how what sets apart those who succeed, both individually and collectively, is how we navigate the grind of incremental progress and the struggles of setback when things don’t go as planned – i.e., the messy middle. This book is an inspirational guide for navigating this most critical part of the journey. And in the end, that journey is usually worth it. As Scott aptly puts it, “some of the most important and memorable parts of life are the ones that have taken the longest.”

This is one of those books you must read if you're its target audience. It IS boring and it IS long, but the information it has, the ideas it gives will all help you achieve your dreams.