For a large part of my career, I worked inside a deeply Microsoft-oriented environment. Outlook was the centre of gravity. SharePoint was the document layer. Microsoft Teams became the collaboration backbone. PowerPoint, Excel and the broader Microsoft stack shaped not only how we worked, but how we thought about work.
Recently, I moved into a very different setup, one that relies far more heavily on tools such as Slack, Notion and Google Workspace, with Microsoft appearing only at the margins when an external constraint requires it. The shift has been more than operational. It has been cultural. And the more time I spend inside this alternative ecosystem, the more convinced I become that the real difference between Apple and Microsoft is not about devices or branding, but about design philosophy and what it signals about how much a company values the lived experience of its users.
Teams and SharePoint – Architecture as Hierarchy
When I refer to design, I am not talking about surface aesthetics. I am talking about how a product structures human interaction, how much cognitive effort it demands, and whether it reduces or increases friction in everyday work. Design in that sense is strategic. It reflects priorities, incentives and power structures inside the organisation that built the software.
Microsoft’s tools, particularly in enterprise environments, often feel as though they are designed to mirror organisational structure. Hierarchy is visible. Permissions are layered. Governance is foregrounded. The architecture frequently resembles the company itself.
This becomes especially clear in the interplay between Teams and SharePoint. Conversations sit inside channels which sit inside teams which map onto departments. Files live in SharePoint libraries that are technically powerful but often conceptually opaque to the average user. Content surfaces in tabs, chats and document views that require you to understand the underlying system in order to navigate it confidently.
None of this is accidental. It reflects an enterprise-first worldview in which compliance, control and visibility are paramount. The system is comprehensive and capable. But the cognitive overhead required to operate within it can be surprisingly high.
Slack and the Alternative Stack – Flow Over Control
By contrast, Slack feels structurally simpler and intentionally lighter. Conversations live in channels. Threads exist to manage noise without fragmenting context. Search is fast and reliable. The mental model is consistent. You do not need to hold the company’s hierarchy in your head in order to participate.
The same is broadly true of Notion and Google Workspace. Notion privileges clarity and flexibility over rigid structure. Google Docs and Sheets feel immediate and accessible rather than administratively complex. The tools assume competence. They assume that people want to get on with the work rather than navigate the system.
This difference may seem subtle, but over time it compounds into culture. Software encodes values. When your primary collaboration environment foregrounds governance and visibility, the experience of work tilts in that direction. When it foregrounds clarity and conversational fluidity, the organisation feels different.
Design Culture Is Organisational Culture
Behold, what is this modern usable device?
This is where Apple’s broader design culture becomes relevant. Apple has historically behaved as though usability is not an optional layer applied after engineering, but a core constraint around which engineering must organise itself. Simplicity is defended. Friction is treated as a failure to be resolved rather than an unavoidable by-product of complexity.
Microsoft, particularly in enterprise contexts, often appears to optimise for feature completeness and compatibility across vast organisational landscapes. That approach produces powerful systems, but it can also produce products that feel heavy and administratively oriented. The user adapts to the system more than the system adapts to the user.
Here at Geckoboard, our stack includes Slack, Notion, Google Workspace, Zoom, Miro, Ghost, HubSpot, Shortcut, and Claude. None of them are perfect. All involve trade-offs. But collectively they feel oriented towards clarity, speed and autonomy rather than layered oversight.
Over time, that difference becomes material. When tools reduce friction, decisions happen faster. When navigation is intuitive, energy is preserved for substantive thinking. When structure supports rather than dominates, culture shifts towards trust.
This is why I see the Apple versus Microsoft question as fundamentally about design culture. It is not about liking Macs more than PCs (which of course I do 😊). It is about whether usability is treated as a strategic advantage or as a secondary concern behind governance and control.
In knowledge work, attention is scarce and cognitive bandwidth is finite. Every layer of unnecessary complexity extracts a cost. Good design returns that cost to the user.
And in a world where almost all professional interaction is mediated through software, that difference is not cosmetic. It is structural.
A final point about branding – I certainly used to think that Microsoft had a big advantage here that you bought Microsoft Office you knew what it was and therefore it, was your go-to software for most problems. But can that still be said for Microsoft today? Does anyone really understand what Microsoft 365 or Copilot actually mean? What actually is what?! Answers on Slack please..