In 2021 and 2022, product manager Steven Sinofsky wrote a…

…first-person account of what I saw at the PC revolution from the perspective of joining Microsoft as a newly hired software design engineer fresh from graduate school working on developer tools, through my time as a program manager and ultimately leading Office, and then moving to Windows, and everything in between.

Sinofsky called the series Hardcore Software: Inside the Rise and Fall of the PC Revolution. It covers 1989–2012 and somewhere inside over 100 chapters, there is a fascinating six parter about the “ribbon” redesign of Office 2007.

• What is Software Bloat, Really?
• A Tour of “Ye Olde Museum Of Office Past”
• Competing Designs, Better Design
• Progress From Vision to Beta
• First Feedback and a Surprise
• Defying Conventional Wisdom to Finish Office

The first part covers the challenge of the team in 2007, taking stock of Office after almost 25 years of its evolution. (Number of toolbars in 1983: one. Number of toolbars in 2003: 31.) The second part shows great screenshots of all the Office versions from 1.0 until then, and the remaining four cover the Ribbon redesign process.

Regardless of how you feel about Microsoft Office today, and whether you consider the Ribbon interface a success, it’s a perfect weekend read as it covers universal challenges of software complexity and change management.

It’s such a potent series I’m sure we’ll come back to it. It covers a lot, including – in the first part – wrestling with a definition of bloat or complexity, which in the context of Office was less about the number of functions available, and more about mastery:

[…] In practice, bloat comes from the fact […] that Office does so many things that customers just assume the product can do whatever they need it to do. Despite that fact, customers have no idea how to make the product do what they need. This feeling of helplessness that leads to frustration. […]

Bloat is owning a product that you cannot master.

This below is a great observation about the perils of an idea of a “simple mode,” which Sinofsky argues is always a leaky abstraction:

We tried reducing bloat by hiding features […], but that only added to the mystery of the product. Mac, Windows, and Office all went through periods of “simple means fewer” and tried mechanisms such as short menus, simple mode, or adaptive toolbars. But that frustrated or confused people. No one really wanted to use a simple mode and there was always one command missing that was needed, so simple mode became a complicated way to do that one thing that made someone’s work unique.

It was great to see this argument for a broad definition of a bug, as it slides exactly into my post from a while back:

Ages ago in ancient Microsoft history there was a debate on the original apps team about what it means for something to be a bug. Is it a crash? Is it data loss? Is it a typo in an error message and so on? Out of that was created a notion of bug severity, a measure for how serious a bug might be from losing all data all the way to simple cosmetic issues. However, when it came to talking about bugs with product support or ultimately customers the definition of a bug was very simple “a bug is any time the software does not do what a customer expects”. This definition created a discipline of documenting everything reported about the product and always making sure every issue was looked at, even if a code change did not result. The key lesson was how helpful an expansive definition was.

There are also observations and research about how users “debug” the product to make it achieve something they know is possible, but they don’t know how:

We called the futzing document debugging, and it created a frustration that the product was powerful yet overwhelming. People believed a specific result was achievable but getting from point A to B seemed impossible or unlearnable.

And some about the challenges of figuring out what features people use:

[…] Most people didn’t know or care what buttons they clicked on or menus they chose so long as it was working for them—and that meant when asked, “Did you use X?” most people couldn’t recall. To a skeptical press or IT manager (and they all were) that meant unused features.

I should stop quoting and let you read in peace. But, check this out. Lisa wasn’t the only one having linguistic fun:

Early keyboard shortcuts were simple, like using Ins(ert) key to copy text from the scrap (clipboard).

Scrap!?

I added a table of contents UI to the most elaborate essays on my site, and then wrote about some of the design details and choices I made there. Let me know if this is an interesting case study! I tried to do something new here with tons of mini videos.

At the bottom, I will also be collecting other implementations I see that are interesting alternatives to my approach.

I hope it’s okay for me to link to my work once in a while.

Today, I published a photo essay about my favourite tech museums. A lot of it doesn’t have to do with software, but in general it’s about craft and good user experience in this specific context.

If you are interested specifically in software, the ACMI part has some of good examples of integration of software in invisible, delightful ways.

I hate most font reveals; they’re written in a pretentious, corporate-meets-Design-with-capital-D way that’s devoid of any value or meaning or feeling, with the requisite highly polished motion graphics that feel pretty like empty sugar calories. They did feel like written by AI before that became a meme.

This feels like the opposite: an actual personal font announcement of Shantell Sans that made me feel things. From Shantell Martin:

When I was 20 or 21, I found out that I was dyslexic. When I started my art degree at Central Saint Martins in London, I was in an environment where it felt like the majority of people were dyslexic. I was instantly part of a cool group of creative people. However, I was disappointed about the amount of teachers who had never spotted my reading challenges. Instead of supporting me to learn to read and write, they punished me.

What I liked about this post is that it hands the mic off to other involved people: Stephen Nixon who “produced” the typeface, and Anya Danilova who took care of the Cyrillic side. It’s a simple technique, but I feel much more effective than doing the “oral history” a.k.a. “journalistic” approach of different people having various quotes interspersed. It can work, but only if you do it really well. Almost no one does it really well.

There’s just so much to love here. The motion graphics are actually useful, informative, and allow you to learn things! Even the “in use” photographs are delightful and don’t feel arbitrary.

Just well done all around.

(Also, I hate Comic Sans, so having something new in the same vein will be genuinely useful.)