Chance of a Nighttime — Hunches and Product Leadership

Darrel Ronald
18 min readSep 9, 2019


This is Part 3 of a series on shifting from Services Leader to Product Leader. Here you can read Part 1 — The Dead-End of Professional Design Services and Part 2 — Hustle! Hustle! Hustle! You can also read Crash Landing, an interlude in the series reflecting on many years ‘working globally’.

Nighttime in Pearl Hill Hawker Centre, Singapore. Photo by author

…chance favours the prepared mind — Louis Pasteur

It has been a winding, challenging and at times lonely route through the night to my decision to move towards Product Leadership. It is really the result of actively following multiple hunches over the years towards discovery. Likewise it is has been a process of entrepreneurship and experimentation; research and reading; and of actively accumulating means without a predefined end.

Service Leadership vs Product Leadership

So on what spectra do we see the key differences between Services and Products?

  1. Services are typically one-off solutions applied to an unbounded problem domain, while Products are typically repeatable and scalable solutions applied to a bounded problem domain. [Spectrum: Specificity]
  2. Services tend to solve messy open-ended challenges that do not fit standard definitions of a solution workflow. Products tend to solve clean closed-ended challenges that do fit standard definitions of a solution workflow. [Spectrum: Algorithmic Complexity]
  3. Services apply a lot of tacit knowledge, whereas Products apply a lot of explicit knowledge. [Spectrum: Knowledge Coherence]
  4. Services tend to work with Clients according to a specific task within a specific contractual framework. Products tend to work for Customers on a general set of tasks within a general terms and conditions contractual framework. [Spectrum: Service Intimacy]

Technology Product Leadership — Let’s Go!

Beyond these key differences, there is a lot of commonality between leadership skills, so I will jump right in to explore how I’ve been both consciously and unconsciously developing these skills over the past years. The consensus today is that technology product leadership lives in at the intersection between Business, User Experience, Technology.

Jeff Koons with his Rabbit which set a selling record for a living artist, purchased for over $91 million. Photo by EPA

The best way to predict the future is to invent it — Alan Kay


In Part 2 of this series, Hustle! Hustle! Hustle! I detail 3 key ventures I worked on between 2008 and 2019. Here I outline their application to Product Leadership.

IMD Executive MBA — In February 2019 I started the first of three modules in the IMD EMBA program. It is a fantastic experience so far and I’m excited to continue on the program in the coming years. I especially learned how to approach business questions from the lens of other industries and profoundly broadened my understanding of finance, marketing, strategy, supply chain, ventures and innovation. The EMBA cohorts have an average age of 40 with 15+ years of experience and from 25+ nationalities; in every exchange you are surrounded by decades of experience and diversity of views.

Vision & Entrepreneurship — In Part 2 I dive deeper into three key ventures at: Open Form Architecture (team entrepreneurship), Spatiomatics (individual entrepreneurship), and KCAP (intrapreneurship). In all cases it was my main responsibility to create a clear vision and mission: What are we doing? Why are we doing it? and How will we succeed? Over the years I have shown an instinct for marketing and branding; I can confidently develop branding and manifestos. Some examples of band names: Nothing Days, Fallen Short; some company names: Open Form Architecture, Spatiomatics, Computable Cities; some publication titles: AUM Design Extra, Anarcho-Urbanism, In Every Skyscraper There is Someone Going Mad.

Prairie Storm in Canada. Photo by storm chaser Nevin deMilliano

Foresight and Business Strategy — the combination of foresight and strategy is one of my favourite things. Geography (including meteorology) was my favourite class in high school; growing up on the prairies of Manitoba I would look out at the sky and practice reading the weather. I focused on cloud formation patterns at different elevations, the vector of wind movements and the travel of rain pockets. This was my training in methodology for reading urban culture, watching technology evolve and thinking critically about what indicators have real meaning in society. When I work on foresight in my own work, or for others such as BMW Radhub, I approach the future like the weather and my strategy emerges as the context changes.

Managing strictly by numbers is like painting by numbers. — Ben Horowitz

Customer Focus — Over 14 years managing clients in 19 different countries on design projects, I have learned inside-out how to develop an empathetic relationship with their specific and unique challenges. Every client and their business culture requires a unique approach in order to: understand their needs; how to read between the lines; how to interview them; how to define problem questions; and how to interpret contextual information so as to provide innovative solutions. It is this area of customer intimacy where an important difference lies between services and products. With services, it is extremely intimate; with products, it can be less so. In technology products the challenge is to create customer intimacy at scale across cultures and situations.

Stakeholders — I have lots of experience with heterogeneous stakeholder groups with divergent interests which can be very very challenging on large-scale complex urban design projects. On some projects, I would manage up to 5 different agencies sitting at the table to discuss and negotiate a large project. A project will also be reviewed by the public and by news media, by commercial developers and by other industry stakeholders. My challenge then is to magically combine these layers of input into an elegant, innovative development proposal that is achievable financially and politically over a long-term process under threat from as-yet unknown challenges and risk factors. With Product Leadership the stakeholder groups will typically be more homogenous with shared interests, but the principles for managing them are universal.

Leadership — according to my teammates I’m an honest and open leader. I aim to align and motivate teams through inspiration. I outline goals and outcomes and leave space for the team to excel in their own way within the framework of the business. I jump in where needed, no task or detail is outside my scope of responsibility if it jeopardizes the quality and success of our team’s work. I share my knowledge and expertise freely and happily sit with team members to learn, teach or train.

Simplicity is the ultimate sophistication. — Leonardo da Vinci
(attributed to him, but nobody can prove it!)

Product Vision —I’m experimenting a lot with this lately. Product vision is an iterative process of discovery that isn’t necessarily an individual task. I have developed a number of internal products and prototype products for business customers as part of the KCAP Computational Design team. I have developed multiple product prototypes with Spatiomatics to test with customers. Likewise I participate in product vision workshops with other entrepreneurs that I’ve met over the years to brainstorm and test product opportunities. In addition, I will soon run a series of re-engineering or re-designing experiments (as a critical learning process) for current products on the market that I think can be improved— some of the experiments will be around UX/UI and others around business model or functionality. This should be fun.

If you want to make enemies, try to change something — Woodrow Wilson

Change Management At KCAP I was selected to form a small “core team” which was responsible for implementing the conclusions of a company repositioning. This involved working with the board to define a scope of work, priorities and timeline; developing a change strategy for the office; implementing improved business processes; organizing stakeholder responsibilities; advocating and pushing change with over 100 staff members in 3 countries. We helped harmonize the internal workings of our different offices and drove cultural change leading to closer relationships between all staff members across the offices. As with all change management, you have many successes and some failures. Our implementation strategy was responsive to what worked and what didn’t and we regularly adjusted tactics over the 2 years of implementation.

We have run out of money. Now we have to think. — Winston Churchill

Finance and Accounting — My finance and accounting skills come from both hands-on experience and studies at IMD. At Open Form Architecture (see Part 2) I setup and managed the accounting; long term budgeting and fiscal targets; profit & loss monitoring; payroll and expenses; billing and accounts receivables. At other design offices I negotiated and managed project contracts that valued up to €1.3 million.

Domain Knowledge — you can argue both ways: domain knowledge is good, or domain knowledge is bad. The problem with domain knowledge is that it comes with hidden biases, potentially narrowed perspectives and assumptions. So you need to start fresh when developing a new product in order to see new opportunities, new ways of framing the research and problem solving or the routes to market. I have a lot of domain knowledge in cities, but the goal is that it fuels rather than impedes innovative product development. For this reason, I’m often tempted to develop products in entirely new domains in order to apply my design thinking expertise from scratch.

Years ago I started researching complexity theory which lead to researching information theory… which lead me to my two programming sabbaticals… which lead me to product leadership. One of my current hunches is around the explosion of new companies sending micro-satellites into space — the author

Work the Hunch — I have been rewarded many times over by following my hunches and intuition. I cultivate my curiosity and continued learning since it has always proven immensely valuable over the years. If you feel that something is heating up in the market, go hunt down the treasure.

Agile Project Management — It’s easy to love the Agile Manifesto. Other than than, I’m not dogmatic on what method of agile to use. I have adapted parts of Scrum into my own work with design teams on projects or when developing computational design products. In the end, refine a technique to make it logical and performant for your organization. A typical use of agile for my design projects: we work in sprint intervals of 2 weeks (minor) and 4 weeks (major); I keep a project roadmap and backlog (timeframe of 2 to 12 months), I monitor burn down rates (high level only); I keep sprint backlogs (usually Asana), we do daily stand-ups. The added complexity for design projects is that we work with external partners, so I might manage up to 5 outside parties; for this I again adapt agile management into a custom process to ensure delivery of all the teams contributions.

Some great business newsletters and podcasts I follow Benedict Evans, AZ16, Ray Dalio, O’Reilly Next:Economy, Stanford ETL, Sifted in addition to many years reading the Financial Times.

Apple Computer tear down. Art by Todd McLellan

If debugging is the process of removing software bugs, then programming must be the process of putting them in — Edsger Dijkstra

Technology and Software

Below I outline some of the key areas of focus needed for working on technology products and how I have been equipping myself for this. Part 4 and Part 5 (to be published) will dive deeper into my two programming sabbaticals.

Computational Thinking — This is one of the things I love most about computer science. Maybe you can code, but more important is understanding Computational Thinking. My obsession with this goes back many years. I first wrote an article in 2010 applying the concept of a Parallel Terraced Scan (from Douglas Hofstadter) to my design process. If you’re looking for a great introduction to computational thinking, Google provides this clear overview.

It is the theory that decides what can be observed. — Albert Einstein

Computer Science — I’ve read 100s of different articles and book excerpts while completing my two sabbaticals (see below, Part 4 and Part 5). In addition to Wikipedia, MDN, Stack Exchange forums, Medium writers and other online sources, these two books have been especially helpful: Effective Computation in Physics by Anthony Scopatz and Introduction to Computation and Programming Using Python by John V. Guttag. For example, when I started to work with Google Maps APIs, I needed to understand Object Oriented Programming (OOP) in order to understand the design patterns.

Mathematics — I first studied Vector Geometry during my architecture undergrad. It has served me well since writing design algorithms especially require an understanding of geometry, vectors and topologies. The book Architectural Geometry is one of the best around for working architects on these topics. Where I want to improve my skills is in Statistics (for analytics), Linear Algebra (for data science) and Graph Theory (for semantic data structures and databases).

Screenshot of a visual script created in Grasshopper for Rhino3D. Script by author
Typical algorithm using visual scripting in Grasshopper for Rhino3D. Script by author.

Algorithms — My deepest experience with algorithms is with decomposing design processes into a set of repeatable products. I typically use the fantastic visual programming of Grasshopper for Rhino3D (screenshot above). Depending on the complexity, I will sketch out the various possible abstractions since many urban design processes are complicated, with diverse rules and inputs, and with dynamic temporal dependencies in the steps of the algorithm. As an example, I developed scripts to automate 5 different urban block typologies in a project but each algorithm was significantly different even though the outcomes were similar typologies with similar ontologies — urban block massing.

Ontologies and Semantics— my experience with this in the context of urban design we need to establish an ontology (aka Knowledge Graph) for elements of the city. If you start to decompose an urban space for example, you need semantic elements that describe these elements in order to create a Graph network that can be contained in a data structure. Surprisingly, this doesn’t readily exist! In architecture there is the Building Information Model (BIM) specification, but it is currently limited to the building scale. There are no international standards for urban design that control the naming of elements and their interrelationships. Due to this, I collaborate with researchers from ETH Zurich at the Future Cities Lab (FCL) in Singapore to develop this further. Once you have a uniform semantic ontology, you can begin to use machine learning. I’m further interested in the emerging work around Urban Information Model (UIM or CIM) or CityBIM which is an important step for potential urban technology products.

Data Structures Data Structures apply to all types of information and correspond to their respective database structure. In the context of urban computing, the mainstream data structures are incomplete for the creation of any type of Urban Information Model (UIM). We have CityGML and GeoJSON which are current industry standards. But the most promising new development is by Hugo Ledoux (and Team at TU Delft in 3D Geoinformation) who created CityJSON. CityJSON offers multiple Levels of Detail (LoDs) and semantic relationships at roughly 6x smaller file sizes.

Cellular automata map in Microsoft Excel defined building structure plans. M.Arch Thesis Project “vetical city” by author.

Simple rules, complex behaviour — Stephen Wolfram

Databases — This is pervasive and foundational to everything digital. I’ve focused my learning on Relational (SQL), Document (NoSQL, MongoDB) and Graph (Neo4j) databases. I understand how they work, when to use them, and have modelled a number of data structures, but I would prefer others to manage this for me. In my grasshopper scripts I typically manage data tracking through the geometry (BIM lite) and/or linked to spreadsheets. I’m still surprised that I cannot find an elegant online solution for rapid setup of databases with front-end interfaces; Airtable is probably the closest thing I guess, even Coda moves in this direction. In the end, I really love spreadsheets (and Stephen Wolfram’s tome A New Kind of Science)— so much so that I used Microsoft Excel and cellular automata to generate part of my final thesis project in Architecture at Université de Montréal (screenshot above).

Web Applications— This has been the focus of my Sabbatical #1 (please read Part 4 in this series). I already had intermediate knowledge writing HTML and CSS code, but needed to dive much deeper into JavaScript, databases and working with APIs.

Python Programming — This has been been the focus of my Sabbatical #2 (please read Part 5 in this series) with two goals: to use Python for software programming and for Data Science. With Python you can get under the hood of most industry leading software.

It takes 20 years to build a reputation and five minutes to ruin it. If you think about that, you’ll do things differently. — Warren Buffet

Security— This is one of the harder topics to grasp and master due to its complexity and rapid evolution. I don’t yet understand all the key issues here and there is proof throughout the industry that even professional programmers are ignorant and/or negligent. We clearly need more White Hat hackers and perhaps more open source security solutions. You can totally ruin your company if you screw this up, especially with respect to the ambitious new governance around the European GDPR which has overnight become the de facto global privacy and security standard.

The map is not the territory. — Alfred Korzybski

Geomatics — I find working with GIS software, geodata, satellite and spatial data in generally to be incredibly frustrating. The main software company, Esri is a disagreeable monopolist with rent-seeking products. QGIS is my preferred open source software with a rich plugin ecosystem, but like Esri products the software is from another era and could be reimagined. The GIS world is still heavy dependent on desktop computers and offline workflows. Open Data portals online are often a messy world of out-of-date or irrelevant material. Overall the GIS workflow can be simplified and made user-friendly, especially to outsiders. Nonetheless there are amazing companies, GIS specialists and open source programmers working on amazing things. FME by Safe stands out as an incredible data engineering tool.

Requirements Engineering — This is something I’ve been spending time learning lately. It’s not complicated, but there are some key best practice lessons and patterns that can be followed to avoid miscommunication. The books I’ve been reading on Software Development are especially Software Engineering by Ian Sommerville and Software Engineering: A Practitioner’s Approach by Roger S. Pressman. I’ve also recently completed the important parts of the Georgia Tech course Software Development Process; it’s good but not great.

Software Development — So far I have not lead a team developing a full software product, but I know how to speak their language and I know how to run teams from 14 years of project management. I suspect that the most critical differences will be in estimating the amount of effort that it could take to complete tasks — this is a tacit skill. For example, I can estimate very accurately the amount of time and effort it can take to finish an architecture and urban design project — this has been learned over the years. So this would be an important learning curve on the first sprints developing a technology product. As with all work, communication and empathy are key, and I think I’ve proven a mastery of these skills.

Your Blind Movement installation by Olafur Eliasson. Photo by Studio Eliasson.

Inspiration is for amateurs — the rest of us just show up and get to work.
— Chuck Close

User Experience (UX) & User Interface (UI)

UX and UI has its origins in visual art, graphic design, motion graphics, industrial design and computer-human interaction. It is built upon the foundational principles of art and design and is essentially a subset of specific design principles and patterns for software and hardware.

Art School — prior to my Bachelor’s of Environmental Design (B.Env.Des.) at the University of Manitoba I completed 2 years in the Bachelor of Fine Arts (BFA). I specialized in photography and printmaking (especially Lithography). This is where I learned the theory and practice of visual communication, the history of art and how to control both analogue and digital media.

Graphic Design — I worked on a number of graphic design projects over the years, working on guerrilla art posters, album covers, publications and websites. In addition, every design project I work on includes the production of books, presentation panels, renderings, physical models and often animations. Graphic communication is one of my key roles in service leadership.

Website Design — I first learned to build websites using (HTML, CSS, JavaScript and Flash) around 1996. Since then I’ve gone on to build about 6 different portfolio websites. At Open Form Architecture I coded the first 2 websites and then guided the design of the 3rd website by an external consultant. At KCAP I assisted the rapid interim redesign of (simplify navigation, update the typography, introduce responsiveness and make imagery more prominent) and I also give input on the functionality, content and design of the new website (in progress) and who to hire to build it. Please see Part 4 in this series about Web Applications.

Blogs — I have worked on at least 4 blogs using Wordpress, including (co-editor, v1.0 design input), the OFA blog (content strategy, UI design, deployment and maintenance), and the internal KCAP intranet (content strategy, UI design and deployment).

Information Design In every design project I’ve worked on there is a need for rich information graphics. In addition, I also work on the information graphics for academics to find simple ways to express complex information (ex. visualizing global healthcare processes).

The skill of writing, and the differences between writers, lies in the creation of a context where other people can think. — Edwin Schlossberg

Publishing working in journalism for newspapers and magazines has taught me a lot over the years: the power of language, how to tell a story, how to write fast and focused, how to engage readers. I first started writing exhibition reviews at my university newspaper (The Manitoban), then I won a grant to create a design publication (AUM Design Extra), then I started writing for architecture magazines (Warehouse, OnSite), then I made some art books, and then I co-founded the design news website (2005–2007) and now I publish stuff on Medium. I love the process of developing a content strategy and trying to seduce and inspire my readers.

Storytelling — This is embedded in all the work I do. As in this series, I prefer to communicate through the fusion of image and text. I always seek to tell a story that conjoins multiple parallel threads that are naturally repellent or divergent.

Technology is the answer. But what was the question? — Cedric Price

Useability and User Documentation — since I started working with computational design tools and writing user scripts products and design workflows, user experience and user interface is a key issue. This is essentially product development for internal use. My main OKRs are the ease of use (delight reported by users in interviews and surveys), the time saved (in hours and days), and the simplification of process (typically measured by design steps taken, clicks needed, reduction of software needed, cost reduction, etc.). I always develop user documentation to spread the tools in the office: a) the script has embedded text documentation and b) I keep a script database for quick filtering and c) I post a detailed use case on the company intranet.

Prototyping — I’ve tested InVision App (before they released InVision Studio), but have worked mostly with Adobe XD since I have deep working knowledge of Adobe InDesign, Photoshop, and Illustrator (products I’ve used for over 20 years).

Workshops with — With I frequently join product and business strategy workshops. They’re developing a product for crowdlearning that can run within your organization for internal training or run publicly through the offcourse site. Together we work on market opportunity and use cases, customer personas and user stories.

Some great UX/UI newsletters I follow— Smashing Magazine, Refactoring UI, Dribble, LearnUI, UX Collective, Interaction Design Foundation, Hacking UI, Facebook Design

Drawing by Emily Flake, The New Yorker

If you don’t underestimate me, I won’t underestimate you — Bob Dylan

Product Leadership — Give Me a Minute!

The last piece of the puzzle in my upskilling is to learn from a few great product leaders. I plan to attend one or two on-campus training workshops this fall:

  • Product Strategy and Product Roadmap Training with Roman Pichler in London — if Brexit doesn’t cause too much chaos.
  • Product Management Foundations with Product School in Amsterdam — planning to do this fall.

There are many other popular offerings on campus or online, such as Product School, Coursera or Udemy, but I don’t have plans yet for these. In my situation it’s smarter to follow a reputable on-campus training workshop and then just start developing your own products.

Helden Wie Wir #2. Artwork by author

Great Reading, Watching, Listening

If you are also undergoing a transition to Product Leadership, this is a handful of specific product books I highly recommend— by no means an exhaustive list:

Coming soon in this series I will tell the story of my two sabbaticals learning how to: build web applications (Part 4) and code with python for software and data science (Part 5).



Darrel Ronald

Founder of Spatiomatics. Creator of the SIMO App for Urban Development. Architect, Urban Designer, Technologist, Entrepreneur.